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Here is a chemical reaction formula: Reactants are aryl halide:B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2)Cl)C(=O)OC, amount is: 0.0014799999771639705 MOLE;amine:C1=CC=C(C=C1)N, amount is: 0.0017800000496208668 MOLE,Reagents are Base:[O-]P(=O)([O-])[O-].[K+].[K+].[K+], amount is: 0.0020800000056624413 MOLE,Solvents are Solvent:COCCOC, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)(C)P(C(C)(C)C)C(C)(C)C, amount is: 4.450000051292591e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 1.4799999917158857e-05 MOLE.Products are 0:B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2)NC3=CC=CC=C3)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: aniline (0.162 mL, 1.78 mmol) was added to methyl 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (440mg, 1.48 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (13.59 mg, 0.01 mmol), tri- tert-butylphosphine (10.80 µL, 0.04 mmol) and potassium phosphate (441 mg, 2.08 mmol) in degassed DME (6 mL) at 20°C under nitrogen. The reaction was stirred at 100 °C for 2 days. The reaction mixture was diluted with Et2O (50 mL), and washed sequentially with water (50 mL) and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated. The crude product was purified by flash silica chromatography, elution 10 to 60% EtOAc in heptane. |
Here is a chemical reaction formula: Reactants are aryl halide:B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2)Cl)C(=O)OC, amount is: 0.0030300000216811895 MOLE;amine:C1=CC=C(C=C1)N, amount is: 0.003949999809265137 MOLE,Reagents are Base:[O-]P(=O)([O-])[O-].[K+].[K+].[K+], amount is: 0.000455000001238659 MOLE,Solvents are Solvent:COCCOC, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)(C)P(C(C)(C)C)C(C)(C)C, amount is: 0.000455000001238659 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.00015199999324977398 MOLE.Products are 0:B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2)NC3=CC=CC=C3)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: aniline (0.360 mL, 3.95 mmol) was added to methyl 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (900 mg, 3.03 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (139 mg, 0.15 mmol), [Reactants] and potassium phosphate (1546 mg, 7.28 mmol) in degassed DME (10 mL) at 20°C under nitrogen. The reaction was stirred at 100 °C for 24 hours. The reaction mixture was allowed to cool then filtered through celite, washing with ethyl acetate. The filtrate was evaporated under reduced pressure to give a brown residue. Not progressed any further. |
Here is a chemical reaction formula: Reactants are amine:CC1=C(C2=C(N1C)C=CC(=C2)N)Cl, amount is: 0.0002749999985098839 MOLE;aryl halide:CC1=NN(C=C1CN2CC(C2)O)C3=NC(=NC=C3)Cl, amount is: 0.0002500000118743628 MOLE,Reagents are Base:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0007510000141337514 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C, amount is: 2.499999936844688e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 1.249999968422344e-05 MOLE.Products are 0:CC1=C(C2=C(N1C)C=CC(=C2)NC3=NC=CC(=N3)N4C=C(C(=N4)C)CN5CC(C5)O)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 40 mL scintillation vial charged with 3-chloro-1,2-dimethyl-1H-indol-5-amine (53.6 mg, 0.28 mmol), 1-((1-(2-chloropyrimidin-4-yl)-3-methyl-1H-pyrazol-4-yl)methyl)azetidin-3-ol (70mg, 0.25 mmol), palladium(II) acetate (2.81 mg, 0.01 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (x--phos) (11.93 mg, 0.03 mmol) and Dioxane (3 mL) After being degassed by nitrogen bubbling , the reaction mixture was heated to 100 °C for 5 hours. LCMS analysis indicated no desired product and chloropyrimidine starting material was decomposed. The reaction mixture was discarded. Need to reverse the sequence. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC=C(C(=C1)Cl)Br, amount is: 0.0052200001664459705 MOLE;amine:C1CNCCN1, amount is: 0.015699999406933784 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.007829999551177025 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.0002610000083222985 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.0002610000083222985 MOLE.Products are 0:C1CN(CCN1)C2=CC=CC=C2Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred sol of 1-bromo-2-chlorobenzene (0.606 mL, 5.22 mmol) in toluene (10 mL) was added Pd2(dba)3 (0.239 g, 0.26 mmol), BINAP (0.163 g, 0.26 mmol), sodium tert-butoxide (0.753 g, 7.83 mmol) and piperazine (1.350 g, 15.67 mmol) and the resulting sol was heated at 110 °C for 16h. Cooled to rt, filtered through a celeite pad, volatiles were evaporated off and residue was column chromatographed (DCM:MeOH 90:10) to afford 1-(2-chlorophenyl)piperazine (0.450 g, 43.8 %) as a gum. |
Here is a chemical reaction formula: Reactants are amine:C1CNCCN1, amount is: 0.015699999406933784 MOLE;aryl halide:C1=CC=C(C(=C1)Cl)Br, amount is: 0.0052200001664459705 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.007829999551177025 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.0002610000083222985 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.0002610000083222985 MOLE.Products are 0:C1CN(CCN1)C2=CC=CC=C2Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred sol of 1-bromo-2-chlorobenzene (0.606 mL, 5.22 mmol) in toluene (10 mL) was added Pd2(dba)3 (0.239 g, 0.26 mmol), BINAP (0.163 g, 0.26 mmol), sodium tert-butoxide (0.753 g, 7.83 mmol) and piperazine (1.350 g, 15.67 mmol) and the resulting sol was heated at 110 °C for 16 h. Filtered through a celeite pad & crude mixture was purified by column chromatography to afford (DCM:MeOH 90:10) to afford 1-(2-chlorophenyl)piperazine (0.600 g, 58.4 %) as a brown gum. |
Here is a chemical reaction formula: Reactants are amine:CC1CNC1, amount is: 0.004689999856054783 MOLE;aryl halide:C1=CC(=CC=C1Br)Br, amount is: 0.004689999856054783 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.011300000362098217 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 9.380000119563192e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 4.690000059781596e-05 MOLE.Products are 0:CC1CN(C1)C2=CC=C(C=C2)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-methylazetidine (0.5 g, 4.69 mmol), diacetoxypalladium (10.53 mg, 0.05 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.058 g, 0.09 mmol) and cesium carbonate (3.67 g, 11.26 mmol), degassed toluene (15 mL) were heated at 100 °C over the weekend. The RM was filtered and washed with EtOAc the filtrate was then concentrated and the crude product purified by flash silica chromatography, elution gradient 20 to 30% EtOAc in heptane. Purest fractions were collected and combined with EN05604-93. The combined product was then recrystalised from EtOAc to give 1-(4-bromophenyl)-3-methylazetidine (0.899 g, 85 %). |
Here is a chemical reaction formula: Reactants are aryl halide:CCOC(=O)C1CC1C(=O)C2=C(C=C(C=N2)Br)OC, amount is: 0.0010000000474974513 MOLE;amine:C1CC1CNC2=CC=C(C3=CC=CC=C32)Cl.Cl, amount is: 0.0012000000569969416 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.002409999957308173 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 7.020000339252874e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 5.0099999498343095e-05 MOLE.Products are 0:CCOC(=O)C1CC1C(=O)C2=C(C=C(C=N2)N(CC3CC3)C4=CC=C(C5=CC=CC=C54)Cl)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Repeat from Patent write up and cf _EN06741-39\Reaction_ **_Aim:-_ **to Prepare target for further use **. NB. the SM is either the (R,R) or (S,S) isomer** ethyl 2-(5-bromo-3-methoxypicolinoyl)cyclopropanecarboxylate (0.329 g, 1.00 mmol), 4-chloro-N-(cyclopropylmethyl)naphthalen-1-amine, HCl (0.323 g, 1.20 mmol), PALLADIUM(II) ACETATE (0.011 g, 0.05 mmol), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (0.044 g, 0.07 mmol) and cesium carbonate (0.784 g, 2.41 mmol) were mixed in toluene (16 mL), purged with nitrogen and stirred in a sealed tube at 70 °C for 19 hours. The reaction mixture was diluted with EtOAc (20 ml), filtered through a celite pad and concentrated to give 902 mg brown oil. TLC (1 : 1 - EtOAc : n-heptane) see diagram UV only The residue was absorbed onto a samplet and purified on a 25 g Biotage SNAP column, eluting with a step-wise gradient from 0 : 10 to 4 : 6 EtOAc : n-heptane using a Thomson pump collecting 25 ml fractions. Pure fractions were evaporated to give 318 mg of orange solid - the product eluted with the 4 : 6 mixture. The front spot was probably binap bis oxide LCMS (pH = 3) Rt = 1.66 min (85% by UV), m/z: 479 (MH+). 1H NMR (DMSO-d6) - looks ok - Aromatics are ok - aliphatics more or less ok but 1 proton missing but there are a number of small peaks as well! **_Conclusion:_ \- **OK to use for further reactions - See EN06995-01 |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC(=CN=C1)CN2C=CC3=C2C=C(C=C3)Br, amount is: 0.004530000034719706 MOLE;amine:CC(C)(C)OC(=O)N, amount is: 0.0067900000140070915 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0009510000236332417 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C, amount is: 0.0009510000236332417 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0003169999981764704 MOLE.Products are 0:CC(C)(C)OC(=O)NC1=CC2=C(C=C1)C=CN2CC3=CN=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 6-bromo-1-(pyridin-3-ylmethyl)-1H-indole (1.3 g, 4.53 mmol), cesium carbonate (2.213 g, 6.79 mmol), tert-butyl carbamate (0.796 g, 6.79 mmol), dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.453 g, 0.95 mmol) and PALLADIUM(II) ACETATE (0.071 g, 0.32 mmol) were placed under a nitrogen atmosphere. dry degassed dioxane (20 mL) was added and the reaction was warmed to 110 °C (using microwave). After reaction completion (3h) the the reaction was diluted with EtOAc(20mL) and water (10mL) and the organic layer was separated. The aqueous layer was washed with a further portion of EtOAc(10mL) and the combined organic layers were dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 30 to 70% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 1-(pyridin-3-ylmethyl)-1H-indol-6-ylcarbamate (1.200 g, 82 %) as a colourless gum. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC(=CN=C1)CN2C=CC3=C2C=C(C=C3)Br, amount is: 0.0003480000013951212 MOLE;amine:CC(C)(C)OC(=O)N, amount is: 0.000522000016644597 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.000522000016644597 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C, amount is: 7.309999637072906e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 2.4400000256719068e-05 MOLE.Products are 0:CC(C)(C)OC(=O)NC1=CC2=C(C=C1)C=CN2CC3=CN=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 6-bromo-1-(pyridin-3-ylmethyl)-1H-indole (0.1 g, 0.35 mmol), cesium carbonate (0.170 g, 0.52 mmol), tert-butyl carbamate (0.061 g, 0.52 mmol), dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.035 g, 0.07 mmol) and PALLADIUM(II) ACETATE (5.47 mg, 0.02 mmol) were placed under a nitrogen atmosphere. dry degassed dioxane (2 mL) was added and the reaction was warmed to 100 °C (using microwave). After reaction completion (2.5h) the the reaction was diluted with EtOAc(20mL) and water (10mL) and the organic layer was separated. The aqueous layer was washed with a further portion of EtOAc(10mL) and the combined organic layers were dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 30 to 70% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 1-(pyridin-3-ylmethyl)-1H-indol-6-ylcarbamate (0.094 g, 83 %) as a colourless gum. |
Here is a chemical reaction formula: Reactants are aryl halide:CCOC(=O)C1=CC=C(C=C1)I, amount is: 0.015599999576807022 MOLE;amine:C1=CC=C(C(=C1)N)Br, amount is: 0.01640000008046627 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.021800000220537186 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.0012499999720603228 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0007789999945089221 MOLE.Products are 0:CCOC(=O)C1=CC=C(C=C1)NC2=CC=CC=C2Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Bromoaniline (1.851 mL, 16.35 mmol) and ethyl 4-iodobenzoate (2.60 mL, 15.58 mmol) were dissolved in toluene (argon bubbled through for 10 min) (80 mL). To the stirred mixture were palladium acetate (0.175 g, 0.78 mmol), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.776 g, 1.25 mmol) and cesium carbonate (7.10 g, 21.81 mmol) added, argon bubbled through the reaction for 2 min and heated then at 100 °C for 3 h. The reaction was not complete (the reaction was checked on a worked-up portion on GCMS and the product was 20% on GCMS). The following were added to the cooled reaction mixture: rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (400 mg) and palladium acetate (100 mg) and then argon bubbled through the reaction for 1 min and heated then at 100 °C overnight. The reaction was checked on a worked- up portion on GCMS => 85% product. The following were added to the cooled reaction mixture: rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (200 mg) and palladium acetate (50 mg) and then argon bubbled through the reaction for 1 min and heated then at 100 °C for 3 h => done. The reaction was poured on a filter-funnel (silica, packed in toluene, eluted with toluene, Rf 0.32). The product came out in fractions 5-8 (Note 1) and they were pooled and the solvent was removed on the rotovap to give ethyl 4-(2-bromophenylamino)benzoate (3.00 g, 60.2 %) as a light brown oil. |
Here is a chemical reaction formula: Reactants are amine:C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C, amount is: 0.0004990000161342323 MOLE;aryl halide:C1=CC(=CN=C1)Br, amount is: 0.0004180000105407089 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.000623999978415668 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 8.320000051753595e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 4.160000025876798e-05 MOLE.Products are 0:C[C@@H]1CN(CCN1C2=CN=CC=C2)C(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: diacetoxypalladium (9.34 mg, 0.04 mmol) and RuPhos (0.039 g, 0.08 mmol) were suspended in 1,4 dioxane (5 mL), degassed and stirred at 50 °C for 10 minutes. Then (R)-tert-butyl 3-methylpiperazine-1-carboxylate (0.100 g, 0.50 mmol), 3-bromopyridine (0.040 mL, 0.42 mmol) and cesium carbonate (0.203 g, 0.62 mmol) were added and the reaction mixture was stirred at 100 °C for 16 h. LCMS showed only 5% conversion to desired product. This was part of a screen and Ruphos, sodium tert-butoxide in toluene gave far better conversion so this was abandoned. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC(=CN=C1)Br, amount is: 0.0063299997709691525 MOLE;amine:C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C, amount is: 0.00949000008404255 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.00949000008404255 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.00031599999056197703 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.00015799999528098851 MOLE.Products are 0:C[C@@H]1CN(CCN1C2=CN=CC=C2)C(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.145 g, 0.16 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.183 g, 0.32 mmol) were added to a mixture of Sodium tert-butoxide (0.912 g, 9.49 mmol), 3-bromopyridine (0.610 mL, 6.33 mmol),(R)-tert-butyl 3-methylpiperazine-1-carboxylate (1.901 g, 9.49 mmol) and toluene (20 mL) under nitrogen. The mixture was heated at 85 °C for 16 hours before being cooled to RT and filtered through celite. The filtrate was concentrated and the reaction mixture was seperated by flash silica chromatography, elution gradient 20 to 40% EtOAc in heptane. No product was isolated. . |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC(=CN=C1)Br, amount is: 0.004989999812096357 MOLE;amine:C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C, amount is: 0.004989999812096357 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.00749000022187829 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 0.000999000039882958 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0004990000161342323 MOLE.Products are 0:C[C@@H]1CN(CCN1C2=CN=CC=C2)C(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: _Repeat of reaction EN05798-78_ Diacetoxypalladium (0.112 g, 0.50 mmol) and dicyclohexyl(2',6'-diisopropoxybiphenyl-2-yl)phosphine (0.466 g, 1.00 mmol) were dissolved in toluene (15 mL) at ambient temperature under nitrogen. The mixture was degassed and purged with nitrogen several times and heated to 50°C for 20 mins. In a separate vessel, were mixed 3-bromopyridine (0.789 g, 4.99 mmol), sodium 2-methylpropan-2-olate (0.720 g, 7.49 mmol), (R)-tert-butyl 3-methylpiperazine-1-carboxylate (1g, 4.99 mmol) and toluene (10 mL). The mixture was degassed and purged with nitrogen several times. The catalyst mixture was added to the reaction vessel and the resulting mixture was degassed and purged with nitrogen, and heated at 100 °C under nitrogen overnight. The reaction mixture was filtered through celite, washing with EtOAc/MeOH. The filtrate was concentrated and the residue purified by flash silica chromatography, elution gradient 20 to 100% EtOAc in heptane. Pure fractions were evaporated to dryness to afford (R)-tert-butyl 3-methyl-4-(pyridin-3-yl)piperazine-1-carboxylate (1.426 g, 103 %) as a pale orange gum. [Rf ~ 0.1 in 1:1 EtOAc/hept] Note: Trace Ruphos contaminating product |
Here is a chemical reaction formula: Reactants are amine:CC1=CN(C=N1)C2=C(N=C(C=C2)N)OC, amount is: 0.00030399998649954796 MOLE;aryl halide:CN1C[C@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3, amount is: 0.00030399998649954796 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0009110000100918114 MOLE,Solvents are Solvent:COCCOC, amount is: 0.0 ,Catalysts are metal and ligand:C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4, amount is: 3.04000004689442e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.04000004689442e-05 MOLE.Products are 0:CC1=CN(C=N1)C2=C(N=C(C=C2)NC3=NC4=C(CN(C[C@H](O4)C5=CC=CC=C5)C)C=C3)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (83 mg, 0.30 mmol) and 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-amine (62.0 mg, 0.30 mmol) in DME (3 mL) was added to a microwave vial containing palladium(II) acetate (6.82 mg, 0.03 mmol), 2-(Dicyclohexylphosphino)biphenyl (10.64 mg, 0.03 mmol) and CS2CO3 (297 mg, 0.91 mmol) under an athmosphere of argon. The resulting mixture was heated to 100°C in a microwave apparatus for 2 h. The reaction mixture was diluted with dichloromethane and methanol and filtered through a plug of Celite. The solvents were evaporated and the residue was purified by HPLC to give 21 mg of the title product (16 % Yield). |
Here is a chemical reaction formula: Reactants are aryl halide:CC1=CC(=C(N=C1)Cl)F, amount is: 0.000686999992467463 MOLE;amine:CC(C)(C)OC(=O)N, amount is: 0.0010300000431016088 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0010300000431016088 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 6.86999992467463e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 6.86999992467463e-05 MOLE.Products are 0:CC1=CC(=C(N=C1)NC(=O)OC(C)(C)C)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: diacetoxypalladium (15.42 mg, 0.07 mmol) and(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (39.8 mg, 0.07 mmol) were added to a degassed mixture of 2-chloro-3-fluoro-5-methylpyridine (100 mg, 0.69 mmol), tert-butyl carbamate (121 mg, 1.03 mmol) and cesium carbonate (336 mg, 1.03 mmol) in dioxane (10 mL) at 21°C. The resulting mixture was stirred at 100 °C for 16 hours.Filtered through celite and adsorbed onto silica. The crude product was purified by flash silica chromatography, elution gradient 0 to 50% DCM in heptane. Pure fractions were evaporated to dryness to afford sm by HNMR Abandoned. .. |
Here is a chemical reaction formula: Reactants are amine:CC(C)(C)OC(=O)N, amount is: 0.0008929999894462526 MOLE;aryl halide:CC1=CC(=C(N=C1)Cl)F, amount is: 0.000686999992467463 MOLE,Reagents are Base:[OH-].[Na+], amount is: 0.0010300000431016088 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 6.86999992467463e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 6.86999992467463e-05 MOLE.Products are 0:CC1=CC(=C(N=C1)NC(=O)OC(C)(C)C)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: diacetoxypalladium (15.42 mg, 0.07 mmol) and(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (39.8 mg, 0.07 mmol) were added to a degassed mixture of 2-chloro-3-fluoro-5-methylpyridine (100 mg, 0.69 mmol), tert-butyl carbamate (105 mg, 0.89 mmol) and 2-chloro-3-fluoro-5-methylpyridine (100 mg, 0.69 mmol) in dioxane (10 mL) at 21°C. The resulting mixture was stirred at 100 °C for 2 hours.Cooled. Adsorbed onto silica. The crude product was purified by flash silica chromatography, elution gradient 10 to 30% DCM in heptane. Pure fractions were evaporated to dryness to afford tert-butyl 3-fluoro-5-methylpyridin-2-ylcarbamate (40.0 mg, 25.7 %) as a cream solid. not pure enough to register .. |
Here is a chemical reaction formula: Reactants are amine:CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)N, amount is: 0.002630000002682209 MOLE;aryl halide:C1CCC2=C(C=NN2CC1)C3=CC(=NC=C3F)Cl, amount is: 0.002630000002682209 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.007899999618530273 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.000526999996509403 MOLE;metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd], amount is: 0.0002629999944474548 MOLE.Products are 0:CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)NC2=NC=C(C(=C2)C3=C4CCCCCN4N=C3)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Tetrakis(triphenylphosphine)palladium(0) (0.304 g, 0.26 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a]azepine (0.700 g, 2.63 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (0.638 g, 2.63 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.305 g, 0.53 mmol) and Cesium carbonate (2.58 g, 7.90 mmol) in 1,4-dioxane (10 mL)Degassed for 5 mins under nitrogen and the resulting suspension was stirred at 120 °C for 17 hours in the microwave reactor. The reaction mixture was partitioned between water (20ml) and ethyl acetate (100ml) filtered and separated. The organics were absorbed onto silica and purified by flash silica chromatography, elution gradient 1:1 EtOAc in heptane. Pure fractions were evaporated to dryness to afford tert-butyl ((1R,3S)-3-((5-fluoro-4-(5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a]azepin-3-yl)pyridin-2-yl)carbamoyl)cyclohexyl)carbamate (0.900 g, 72.4 %) as a white solid. Product is crude so used directly in the next step. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC(=CC=C1Br)Br, amount is: 0.021199999377131462 MOLE;amine:CCOC(=O)C1CCNCC1, amount is: 0.021199999377131462 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.02539999969303608 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.0015899999998509884 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.0005300000193528831 MOLE.Products are 0:CCOC(=O)C1CCN(CC1)C2=CC=C(C=C2)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of ethyl piperidine-4-carboxylate (3.27 mL, 21.20 mmol), 1,4-dibromobenzene (5 g, 21.20 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.485 g, 0.53 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.990 g, 1.59 mmol) and Sodium Tert-Butoxide (2.444 g, 25.43 mmol) in anhydrous toluene (60 mL) was stirred at 85 °C under nitrogen for 16 hours. The reaction was cooled to ambient temperature, diluted with Ether (100 mL) and filtered through celite. The filtrate was evaporated in vacuo to yield crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in heptane. Pure fractions were evaporated to dryness to afford ethyl 1-(4-bromophenyl)piperidine-4-carboxylate (3.91 g, 59.1 %) as a yellow oil. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC(=CC=C1Br)Br, amount is: 0.0061900001019239426 MOLE;amine:COC(=O)C1CCNC1, amount is: 0.0061900001019239426 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.007430000230669975 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.00046499999007210135 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.00015500000154133886 MOLE.Products are 0:COC(=O)C1CCN(C1)C2=CC=C(C=C2)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of methyl pyrrolidine-3-carboxylate (800 mg, 6.19 mmol), 1,4-dibromobenzene (1461 mg, 6.19 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (142 mg, 0.15 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (289 mg, 0.46 mmol) and Sodium Tert-Butoxide (714 mg, 7.43 mmol) in anhydrous toluene (30 mL) was stirred at 85 °C under nitrogen for 4 hours. The reaction was cooled to ambient temperature, diluted with Ether (100 mL) and filtered through celite. The filtrate was evaporated in vacuo to yield crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in heptane. Pure fractions were evaporated to dryness to afford methyl 1-(4-bromophenyl)pyrrolidine-3-carboxylate (513 mg, 29.1 %) as a yellow solid. |
Here is a chemical reaction formula: Reactants are amine:COC(=O)C1CCNC1, amount is: 0.016300000250339508 MOLE;aryl halide:C1=CC(=CC=C1Br)Br, amount is: 0.016300000250339508 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.019500000402331352 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.0012199999764561653 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.00040600000647827983 MOLE.Products are 0:COC(=O)C1CCN(C1)C2=CC=C(C=C2)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of methyl pyrrolidine-3-carboxylate (2.1 g, 16.26 mmol), 1,4-dibromobenzene (3.84 g, 16.26 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.372 g, 0.41 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.759 g, 1.22 mmol) and Sodium Tert-Butoxide (1.875 g, 19.51 mmol) in anhydrous toluene (60 mL) was stirred at 85 °C under nitrogen for 16 hours. The reaction was cooled to ambient temperature, diluted with Ether (100 mL) and filtered through celite. The filtrate was evaporated in vacuo to yield crude product. The crude product was purified by flash silica chromatography, elution gradient 5 to 20% EtOAc in heptane. Pure fractions were evaporated to dryness to afford methyl 1-(4-bromophenyl)pyrrolidine-3-carboxylate (1.460 g, 31.6 %) as a yellow solid. |
Here is a chemical reaction formula: Reactants are aryl halide:CC(=O)NC1=CC(=C(C=C1)OC)Br, amount is: 0.002050000010058284 MOLE;amine:CC(C)(C)OC(=O)N1CCNCC1, amount is: 0.002050000010058284 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.004509999882429838 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 0.00041000000783242285 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00020500000391621143 MOLE.Products are 0:CC(=O)NC1=CC(=C(C=C1)OC)N2CCNCC2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of N-(3-bromo-4-methoxyphenyl)acetamide (0.5 g, 2.05 mmol) dissolved in toluene (5 mL) was treated with tert-butyl piperazine-1-carboxylate (0.382 g, 2.05 mmol), diacetoxypalladium (0.046 g, 0.20 mmol), dicyclohexyl(2',6'-diisopropoxybiphenyl-2-yl)phosphine (0.191 g, 0.41 mmol) and sodium 2-methylpropan-2-olate (0.433 g, 4.51 mmol) in a sealed tube. The resulting mixture was degassed and stirred at 100 °C for 8 hours in a microwave. The mixture was pre-absorbed onto silica. The crude product was purified by flash silica chromatography, elution 50% ethyl acetate in Heptane. Pure fractions were evaporated to dryness to afford intermediate. The intermediate was dissolved in 4M HCl in dioxane (10mL) and stirred at RT overnight. The mixture was evaporated to give N-(4-methoxy-3-(piperazin-1-yl)phenyl)acetamide (0.260 g, 50.9 %) as a tan solid. |
Here is a chemical reaction formula: Reactants are aryl halide:CC1=C(C=C(C=C1)NC(=O)C2=CC3=C(C=C2)OCCO3)NC(=O)C4=CN=C(C=C4)Cl, amount is: 0.00011800000356743112 MOLE;amine:CN1CCN(CC1)CC2=CC(=CC=C2)N, amount is: 0.00017699999443721026 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.00017699999443721026 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 7.080000159476185e-06 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 3.5400000797380926e-06 MOLE.Products are 0:CC1=C(C=C(C=C1)NC(=O)C2=CC3=C(C=C2)OCCO3)NC(=O)C4=CN=C(C=C4)NC5=CC=CC(=C5)CN6CCN(CC6)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 6-chloro-N-(5-(2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamido)-2-methylphenyl)nicotinamide (50 mg, 0.12 mmol),3-((4-methylpiperazin-1-yl)methyl)aniline (36.3 mg, 0.18 mmol),(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (4.10 mg, 7.08 µmol),TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (3.24 mg, 3.54 µmol),sodium 2-methylpropan-2-olate (17.01 mg, 0.18 mmol) in toluene (2 mL)/IPA (0.500 mL)was degassed with nitrogen and heated at reflux for 18 hours.The reaction mixture was filtered and filtered solid washed with ethyl acetate. The organic filtrate was washed with water (50ml), and organic layer dried over Na2SO4, filtered and evaporated. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5µ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford N-(5-(2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamido)-2-methylphenyl)-6-(3-((4-methylpiperazin-1-yl)methyl)phenylamino)nicotinamide (18.10 mg, 25.9 %) as a beige solid. |
Here is a chemical reaction formula: Reactants are amine:C1COCCC1CN, amount is: 0.0008479999960400164 MOLE;aryl halide:C1=CC(=CC(=C1)I)Br, amount is: 0.0008479999960400164 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0012700000079348683 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.00012700000661425292 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 6.359999679261819e-05 MOLE.Products are 0:C1COCCC1CNC2=CC(=CC=C2)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Palladium (II) acetate (14.28 mg, 0.06 mmol) and racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (79 mg, 0.13 mmol) were suspended in toluene (3 mL). The mixture was evacuated and purged with nitrogen, and warmed to 50°C. In a separate vessel, 1-bromo-3-iodobenzene (240 mg, 0.85 mmol), (tetrahydro-2H-pyran-4-yl)methanamine (98 mg, 0.85 mmol) and sodium-t-butoxide (122 mg, 1.27 mmol) were suspended in toluene (3.5 mL). The resulting mixture was evacuated, purged with nitrogen and warmed to 50°C. After ~30 mins, the catalyst mixture was transferred to the reaction vessel. The reaction was evacuated and purged with nitrogen and heated at 80°C overnight. This reaction was combined with EN06953-06 for purification. The mixture was filtered and purified by flash silica chromatography, elution gradient 0 to 40% EtOAc in heptane. Pure fractions were evaporated to dryness to afford 3-bromo-N-((tetrahydro-2H-pyran-4-yl)methyl)aniline (71.0 mg, 31.0 %) as a colourless oil which crystallised on standing. The main impurity was isolated (EN06953-09-02) but this was not identified; assume it is BINAP or the catalyst- ligand complex. |
Here is a chemical reaction formula: Reactants are aryl halide:COC(=O)C1=CC(=CC(=C1)I)Br, amount is: 0.014000000432133675 MOLE;amine:C1=CC=C(C=C1)N, amount is: 0.014000000432133675 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.011900000274181366 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.00139999995008111 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00139999995008111 MOLE.Products are 0:COC(=O)C1=CC(=CC(=C1)Br)NC2=CC=CC=C2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: diacetoxypalladium (0.314 g, 1.40 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.871 g, 1.40 mmol) were added to a degassed mixture of methyl 3-bromo-5-iodobenzoate (4.77 g, 13.99 mmol), aniline (2.55 ml, 13.99 mmol) and cesium carbonate (3.87 g, 11.89 mmol) in toluene (137 ml) under nitrogen. The resulting mixture was stirred at 110 °C for 18 hours. The resulting mixture was evaporated to dryness and the residue was diluted with EtOAc (150 mL), and washed with water (100 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 15% EtOAc in heptane. Pure fractions were evaporated to dryness to afford methyl 3-bromo-5-(phenylamino)benzoate (1.735 g, 40.5 %) as a pale yellow solid. |
Here is a chemical reaction formula: Reactants are amine:C1=CC(=CN=C1)CN, amount is: 0.0005370000144466758 MOLE;aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0009769999887794256 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 5.999999848427251e-05 MOLE.Products are 0:C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CN=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Pyridin-3-ylmethanamine (58.1 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was heated thermally to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Fractions containing product were evaporated to dryness to afford N2-phenyl-N4-(pyridin-3-ylmethyl)pyridine-2,4-diamine (80 mg, 59.2 %) as an off white solid. |
Here is a chemical reaction formula: Reactants are aryl halide:CC1(CC2=NC=C(N2C1)C3=CC(=NC=C3F)Cl)C, amount is: 0.0003760000108741224 MOLE;amine:CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)N, amount is: 0.00045200000749900937 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.001129999989643693 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 7.529999857069924e-05 MOLE;metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd], amount is: 3.7599998904624954e-05 MOLE.Products are 0:CC1(CC2=NC=C(N2C1)C3=CC(=NC=C3F)NC(=O)[C@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Tetrakis(triphenylphosphine)palladium(0) (43.5 mg, 0.04 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-6,6-dimethyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole (100 mg, 0.38 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (109 mg, 0.45 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (43.6 mg, 0.08 mmol) and Cesium carbonate (368 mg, 1.13 mmol) in 1,4-dioxane (5.98 ml). Degassed for 5 mins under nitrogen and the resulting suspension was stirred at 120 °C for 3 hours in the microwave reactor. The reaction mixture was partitioned between water (20ml) and DCM (40ml) and separated using a phase separation cartridge. The organics were absorbed onto silica and purified by flash silica chromatography, elution gradient 0 to 60% EtOAc in heptane. Pure fractions were evaporated to dryness to afford starting material (100mg). |
Here is a chemical reaction formula: Reactants are aryl halide:CC1=CC(=NC=C1Br)Cl, amount is: 0.0004839999892283231 MOLE;amine:CCOC(=O)C1CCNCC1, amount is: 0.0006779999821446836 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 4.8400001105619594e-05 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 4.8400001105619594e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 2.4200000552809797e-05 MOLE.Products are 0:CCOC(=O)C1CCN(CC1)C2=CN=C(C=C2C)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.18 mg, 0.02 mmol) was added to a degassed mixture of ethyl piperidine-4-carboxylate (0.105 mL, 0.68 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine)(xantphos) (28.0 mg, 0.05 mmol) and ethyl 1-(6-chloro-4-methylpyridin-3-yl)piperidine-4-carboxylate and sodium 2-methylpropan-2-olate (65.2 mg, 0.68 mmol) in toluene (3 mL). The resulting suspension was stirred at 100 °C for 20 hours under nitrogen. LCMS indicated little reaction so reaction abandoned. |
Here is a chemical reaction formula: Reactants are aryl halide:CC1=CC(=NC=C1Br)Cl, amount is: 0.0004839999892283231 MOLE;amine:CCOC(=O)C1CCNCC1, amount is: 0.0006779999821446836 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 9.690000297268853e-05 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 9.690000297268853e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 4.8400001105619594e-05 MOLE.Products are 0:CCOC(=O)C1CCN(CC1)C2=CN=C(C=C2C)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of diacetoxypalladium (10.87 mg, 0.05 mmol) and dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (45.2 mg, 0.10 mmol) dissolved in toluene (3 mL) was degassed and heated to 50°C for 30 minutes before adding ethyl piperidine-4-carboxylate (0.105 mL, 0.68 mmol), 5-bromo-2-chloro-4-methylpyridine (100 mg, 0.48 mmol) and sodium 2-methylpropan-2-olate (74.5 mg, 0.77 mmol) under nitrogen. The mixture was heated to 100°C for 2 hours. LCMS indicated little product so reaction abandoned. |
Here is a chemical reaction formula: Reactants are amine:COC1=CC=CC=C1CN, amount is: 0.0005370000144466758 MOLE;aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0009769999887794256 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 5.999999848427251e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.909999941242859e-05 MOLE.Products are 0:COC1=CC=CC=C1CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (2-methoxyphenyl)methanamine (73.7 mg, 0.54 mmol), 4-chloro-N- phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was heated thermally to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Fractions containing product were evaporated to dryness to afford N4-(2-methoxybenzyl)-N2-phenylpyridine-2,4-diamine (90 mg, 60.3 %) as an off-white solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE;amine:COC1=CC=CC=C1CN, amount is: 0.0005370000144466758 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0009769999887794256 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 5.999999848427251e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.909999941242859e-05 MOLE.Products are 0:COC1=CC=CC=C1CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (2-methoxyphenyl)methanamine (73.7 mg, 0.54 mmol), 4-chloro-N- phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was heated thermally to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Fractions containing product were evaporated to dryness and purified by C18 silica chromatography, elution gradient 40 to 70% MeCN in Water + 1% NH4OH. Fractions containing product were evaporated to dryness to afford N4-(2-methoxybenzyl)-N2-phenylpyridine-2,4-diamine (16.00 mg, 10.72 %) as a yellow gum. |
Here is a chemical reaction formula: Reactants are aryl halide:COC1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.00042600001324899495 MOLE;amine:C1=CC=C(C=C1)CN, amount is: 0.0004689999914262444 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0008520000264979899 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 4.999999873689376e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 2.9999999242136255e-05 MOLE.Products are 0:COC1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenylmethanamine (50.2 mg, 0.47 mmol), 4-chloro-N-(4-methoxyphenyl)pyridin-2-amine (100 mg, 0.43 mmol) and sodium 2-methylpropan-2-olate (82 mg, 0.85 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (28.4 mg, 0.05 mmol) and diacetoxypalladium (7.65 mg, 0.03 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was heated thermally to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Fractions containing product were evaporated to dryness to afford N4-benzyl-N2-(4-methoxyphenyl)pyridine-2,4-diamine (77 mg, 59.2 %) as an off-white solid. |
Here is a chemical reaction formula: Reactants are aryl halide:CC1=NN(C=C1C=O)C2=NC(=NC=C2)Cl, amount is: 0.0008980000275187194 MOLE;amine:CC1=C(C2=C(N1C)C=CC(=C2)N)Cl, amount is: 0.0009879999561235309 MOLE,Reagents are Base:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0027000000700354576 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C, amount is: 8.97999998414889e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 4.489999992074445e-05 MOLE.Products are 0:CC1=C(C2=C(N1C)C=CC(=C2)NC3=NC=CC(=N3)N4C=C(C(=N4)C)C=O)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 40 mL scintillation vial charged with 3-chloro-1,2-dimethyl-1H-indol-5-amine (192 mg, 0.99 mmol), 1-(2-chloropyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carbaldehyde (200mg, 0.90 mmol), palladium(II) acetate (10.08 mg, 0.04 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (x--phos) (42.8 mg, 0.09 mmol) and Dioxane (8mL) After being degassed by nitrogen bubbling , the reaction mixture was heated 100 °C for 6 hours. At this stage most of the starting material was consumed. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with water and brine. The organic layer separated, dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography (Isco, Hexane/ethyl acetate, 0-100%, 25 minutes) to give 1-(2-((3-chloro-1,2-dimethyl-1H-indol-5-yl)amino)pyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carbaldehyde (221 mg, 64.6 %) as a yellow solid. LC/MS (2 minute, Acid _CV10.olp method) 381 (M + 1), 1.27 minutes. |
Here is a chemical reaction formula: Reactants are aryl halide:C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)N.C(=O)(C(F)(F)F)O, amount is: 0.00046400001156143844 MOLE;amine:C1=C2C(=CC(=C1F)F)NC(=O)C=C2Cl, amount is: 0.00046400001156143844 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0013899999903514981 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 4.640000042854808e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 4.640000042854808e-05 MOLE.Products are 0:C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)NC3=CC(=O)NC4=CC(=C(C=C43)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-chloro-6,7-difluoroquinolin-2(1H)-one (100 mg, 0.46 mmol) was taken in a microwave tube. Added ((2S,4R)-4-amino-2-methylpiperidin-1-yl)(5-chloro-1-methyl-1H-pyrazol-4-yl)methanone 2,2,2-trifluoroacetate (172 mg, 0.46 mmol), followed by the addition of Palladium (II) acetate (10.41 mg, 0.05 mmol), racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (28.9 mg, 0.05 mmol), Cesium carbonate (111 mL, 1.39 mmol), N,N'-Diisopropylethylamine (242 mL, 1.39 mmol). toluene (10 mL) was added and subjected to microwave with the following parameters. Temperature 140 °C Time 60 minutes After the completion of the reaction, dissolved the compound in methanol and purified by column |
Here is a chemical reaction formula: Reactants are aryl halide:C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)N.C(=O)(C(F)(F)F)O, amount is: 0.004170000087469816 MOLE;amine:C1=C2C(=CC(=C1F)F)NC(=O)C=C2Cl, amount is: 0.0027799999807029963 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.008349999785423279 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.00027799999224953353 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00027799999224953353 MOLE.Products are 0:C[C@H]1C[C@@H](CCN1C(=O)C2=C(N(N=C2)C)Cl)NC3=CC(=O)NC4=CC(=C(C=C43)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: ((2S,4R)-4-amino-2-methylpiperidin-1-yl)(5-chloro-1-methyl-1H-pyrazol-4-yl)methanone 2,2,2-trifluoroacetate (1548 mg, 4.17 mmol) was taken in a 100ml single necked flask equipped with a reflux condenser connected to nitrogen source. Added 4-chloro-6,7-difluoroquinolin-2(1H)-one (600 mg, 2.78 mmol), followed by the addition of racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (173 mg, 0.28 mmol), Palladium (II) acetate (62.5 mg, 0.28 mmol), and Cesium carbonate (668 mL, 8.35 mmol). toluene (60 mL) was added followed by the addition of N,N'-Diisopropylethylamine (1454 mL, 8.35 mmol). The contents of the flask were purged with nitrogen for 5 minutes and heate at 140 °C for overnight. After the completion of the reaction, added methanol, and adsorbed on silica gel, and purified by reverse phase column. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE;amine:C1=CC(=CC=C1CN)F, amount is: 0.0005370000144466758 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0009769999887794256 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 5.999999848427251e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.9999998989515007e-05 MOLE.Products are 0:C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC=C(C=C3)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (4-fluorophenyl)methanamine (67.3 mg, 0.54 mmol), 4-chloro-N- phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was heated thermally to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Fractions containing product were evaporated to dryness to afford N4-(4-fluorobenzyl)-N2-phenylpyridine-2,4-diamine (86 mg, 60.0 %) as an off-white solid. |
Here is a chemical reaction formula: Reactants are amine:C1COCCC1CN, amount is: 0.005350000225007534 MOLE;aryl halide:COC1=CC=C(C=C1)Br, amount is: 0.005350000225007534 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.008019999600946903 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0008019999950192869 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00040099999750964344 MOLE.Products are 0:COC1=CC=C(C=C1)NCC2CCOCC2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Palladium (II) acetate (0.090 g, 0.40 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.464 g, 0.80 mmol) were suspended in toluene (3 mL). The mixture was evacuated and purged with nitrogen, and warmed to 50°C. In a separate vessel, 1-bromo-4-methoxybenzene (1 g, 5.35 mmol), (tetrahydro-2H-pyran-4-yl)methanamine (0.654 mL, 5.35 mmol) and sodium-t- butoxide (0.771 g, 8.02 mmol) were suspended in toluene (7 mL). The resulting mixture was evacuated, purged with nitrogen and warmed to 50°C. After ~30 mins, the catalyst mixture was transferred to the reaction vessel. The reaction was evacuated and purged with nitrogen and heated at 80°C overnight. The mixture was diluted with water (250 mL), and extracted with ethyl acetate (200 mL). The organic was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and crude fractions were evaporated to dryness to afford 4-methoxy-N-((tetrahydro-2H-pyran-4-yl)methyl)aniline (0.270 g, 22.82 %) as a brown oil. |
Here is a chemical reaction formula: Reactants are amine:C1=CC=C(C=C1)CN, amount is: 0.0005370000144466758 MOLE;aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 5.859999873791821e-05 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 5.859999873791821e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.909999941242859e-05 MOLE.Products are 0:C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. 2-Dicyclohexylphosphino-2',6'-di- i-propoxy-1,1'-biphenyl (27.4 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was heated thermally to 100 °C for 30 mins under nitrogen cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by preparative HPLC (Waters SunFire column, 5µ silica, 50 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 0.1% formic acid) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness N4-benzyl-N2-phenylpyridine-2,4-diamine (17.80 mg, 13.23 %) as an off-white solid. |
Here is a chemical reaction formula: Reactants are amine:C1=CC=C(C=C1)CN, amount is: 0.0005370000144466758 MOLE;aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 5.859999873791821e-05 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C, amount is: 5.859999873791821e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.909999941242859e-05 MOLE.Products are 0:C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. Dicyclohexyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (31.5 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was heated thermally to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by preparative HPLC (Waters SunFire column, 5µ silica, 50 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 0.1% formic acid) and MeCN as eluents. Fractions containing product were evaporated to dryness to afford N4-benzyl-N2-phenylpyridine-2,4-diamine (8.50 mg, 6.32 %) as an off white solid. |
Here is a chemical reaction formula: Reactants are amine:C1=CC=C(C=C1)CN, amount is: 0.0005370000144466758 MOLE;aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0009769999887794256 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 5.999999848427251e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.909999941242859e-05 MOLE.Products are 0:C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was heated thermally to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by preparative HPLC (Waters SunFire column, 5µ silica, 50 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 0.1% formic acid) and MeCN as eluents. Fractions containing product were evaporated to dryness to afford N4-benzyl-N2-phenylpyridine-2,4-diamine (72.4 mg, 53.8 %) as an off-white solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE;amine:C1=CC=C(C=C1)CN, amount is: 0.0007820000173524022 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0009769999887794256 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 5.999999848427251e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.909999941242859e-05 MOLE.Products are 0:C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenylmethanamine (84 mg, 0.78 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was heated thermally to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by preparative HPLC (Waters SunFire column, 5µ silica, 50 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 0.1% formic acid) and MeCN as eluents. Fractions containing product were evaporated to dryness to afford N4-benzyl-N2-phenylpyridine-2,4-diamine (85 mg, 63.1 %) as an off-white solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE;amine:C1=CC=C(C=C1)CN, amount is: 0.0005370000144466758 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 5.859999873791821e-05 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C, amount is: 5.859999873791821e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.909999941242859e-05 MOLE.Products are 0:C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. Dicyclohexyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (31.5 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was thermally heated to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by preparative HPLC (Waters SunFire column, 5µ silica, 50 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 0.1% formic acid) and MeCN as eluents. Fractions containing product were evaporated to dryness to afford N4-benzyl-N2-phenylpyridine-2,4-diamine (49.6 mg, 36.9 %) as an off white solid. |
Here is a chemical reaction formula: Reactants are amine:C1=CC=C(C=C1)CN, amount is: 0.0005370000144466758 MOLE;aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 5.859999873791821e-05 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C, amount is: 5.859999873791821e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.909999941242859e-05 MOLE.Products are 0:C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. Dicyclohexyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (31.5 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was thermally heated to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by preparative HPLC (Waters SunFire column, 5µ silica, 50 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 0.1% formic acid) and MeCN as eluents. Fractions containing product were evaporated to dryness to afford N4-benzyl-N2-phenylpyridine-2,4-diamine (56.5 mg, 42.0 %) as an off white solid. |
Here is a chemical reaction formula: Reactants are amine:C1=CC=C(C=C1)CN, amount is: 0.0005370000144466758 MOLE;aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 5.859999873791821e-05 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 5.859999873791821e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.909999941242859e-05 MOLE.Products are 0:C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. 2-Dicyclohexylphosphino-2',6'-di- i-propoxy-1,1'-biphenyl (27.4 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was heated thermally to 100 °C for 1.5 hours under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by preparative HPLC (Waters SunFire column, 5µ silica, 50 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 0.1% formic acid) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness N4-benzyl-N2-phenylpyridine-2,4-diamine (6.50 mg, 4.83 %) as an off-white solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE;amine:C1=CC=C(C=C1)CN, amount is: 0.0005370000144466758 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0009769999887794256 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 5.999999848427251e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.909999941242859e-05 MOLE.Products are 0:C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol)-diacetoxypalladium (8.78 mg, 0.04 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2.00 mL) and sealed into a microwave tube. The reaction was heated thermally to 100 °C for 30 minutes and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford N4-benzyl-N2-phenylpyridine-2,4-diamine (66.4 mg, 49.4 %) as an off- white solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE;amine:C1=CC=C(C=C1)CN, amount is: 0.0005370000144466758 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0009769999887794256 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 5.999999848427251e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.909999941242859e-05 MOLE.Products are 0:C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were added to the reaction mixture in DMA (1 mL). Nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was heated thermally to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Fractions containing product were evaporated to dryness to afford N4-benzyl-N2-phenylpyridine-2,4-diamine (93 mg, 69.1 %) as an off-white solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE;amine:C1=CC=C(C=C1)CN, amount is: 0.0005370000144466758 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0009769999887794256 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 5.999999848427251e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.909999941242859e-05 MOLE.Products are 0:C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol)-diacetoxypalladium (8.78 mg, 0.04 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2.00 mL) and sealed into a microwave tube. The reaction was heated thermally to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford N4-benzyl-N2-phenylpyridine-2,4-diamine (77 mg, 57.0 %) as an off-white solid. |
Here is a chemical reaction formula: Reactants are amine:C1=CC=C(C=C1)CN, amount is: 0.0005370000144466758 MOLE;aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0009769999887794256 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 5.999999848427251e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.909999941242859e-05 MOLE.Products are 0:C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was heated thermally to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Fractions containing product were evaporated to dryness to afford EN06208-42-01 (98 mg, 0.356 mmol, 72.8 %) as an off-white solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0012199999764561653 MOLE;amine:C1=CC=C(C=C1)CN, amount is: 0.001339999958872795 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0024399999529123306 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 0.0001500000071246177 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 9.770000178832561e-05 MOLE.Products are 0:C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenylmethanamine (144 mg, 1.34 mmol), 4-chloro-N-phenylpyridin-2-amine (250 mg, 1.22 mmol)-diacetoxypalladium (21.94 mg, 0.10 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (81 mg, 0.15 mmol) and sodium 2-methylpropan-2-olate (235 mg, 2.44 mmol) were suspended in DMA (2.50 mL) in a partially sealed tube. The reaction was heated thermally to 80 °C for 1 hour, followed by 90°C overnight and cooled to RT. The reaction mixture was filtered through celite using methanol, neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford N4-benzyl-N2-phenylpyridine-2,4-diamine (33.0 mg, 9.81 %) as a brown gum. |
Here is a chemical reaction formula: Reactants are amine:C1=CC=C(C=C1)CN, amount is: 0.0005370000144466758 MOLE;aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0009769999887794256 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 5.999999848427251e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 5.859999873791821e-05 MOLE.Products are 0:C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Phenylmethanamine (57.6 mg, 0.54 mmol), 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol)-diacetoxypalladium (8.78 mg, 0.04 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2.00 mL) in a partially sealed tube. The reaction was heated thermally to 100 °C for 30 minutes and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20g SCX column. The crude product was purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford N4-benzyl-N2-phenylpyridine-2,4-diamine (7.60 mg, 5.65 %) as an off-white solid. |
Here is a chemical reaction formula: Reactants are amine:CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2, amount is: 0.002520000096410513 MOLE;aryl halide:COC1=CC=CC=C1Br, amount is: 0.002520000096410513 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.004029999952763319 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.00010099999781232327 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 5.0400001782691106e-05 MOLE.Products are 0:CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2C3=CC=CC=C3OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.046 g, 0.05 mmol) and rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.063 g, 0.10 mmol) were mixed together and evacuated and purged with nitrogen 3 times. toluene (24.91 ml) was added and the resulting mixture heated to 50°C for 10 minutes. In a second reaction vessel was mixed sodium tert-butoxide (0.387 g, 4.03 mmol), (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.500 g, 2.52 mmol), 1-bromo-2-methoxybenzene (0.314 ml, 2.52 mmol) and toluene (24.91 ml). The mixture was evacuated and purged with nitrogen 3 times. The solution of catalyst was added to the reaction mixture and the resulting mixture was heated at 105 °C for 16 hours. The reaction mixture was cooled to RT and filtered through celite and evaporated. The crude product was purified by flash silica chromatography, elution gradient 100% DCM. Pure fractions were evaporated to dryness to afford (1S,4S)-tert-butyl 5-(2-methoxyphenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.529 g, 68.9 %) as a yellow gum. |
Here is a chemical reaction formula: Reactants are amine:C1CCNCC1, amount is: 0.0022499999031424522 MOLE;aryl halide:C1=CC(=C(C=C1C(=O)O)Cl)Br, amount is: 0.001500000013038516 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0022499999031424522 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 4.999999873689376e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 1.4999999621068127e-05 MOLE.Products are 0:C1CCN(CC1)C2=C(C=C(C=C2)C(=O)O)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-bromo-3-chlorobenzoic acid (0.353 g, 1.5 mmol), piperidine (0.234 mL, 2.25 mmol), and sodium tert-butoxide (0.216 g, 2.25 mmol) were stirred together under N2 and heated to 80 °C. Pd2(dba)3 (0.014 g, 0.015 mmol), and BINAP (0.031 g, 0.05 mmol) were mixed in toluene (2 mL) and then added to the mixture and stirred at 110 °C overnight. LCMS showed a very small amount of desired product (~2%). The reaction mixture was degassed with N2 for 30 minutes, then addtional Pd/ Binap was added. The reaction was again heated to 110 C. LCMS showed a small amount of desired product (~10%) but mostly still starting material. The desired product was not isolated from this reaction. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC2=C(C=C1Br)NN=C2, amount is: 0.006089999806135893 MOLE;amine:C1CCNC1, amount is: 0.007340000011026859 MOLE,Reagents are Base:[Li+].C[Si](C)(C)[N-][Si](C)(C)C, amount is: 0.014999999664723873 MOLE,Solvents are Solvent:C1CCOC1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 0.00012199999764561653 MOLE;metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.C1=CC=C([C-]=C1)CCN.[Cl-].[Pd+2], amount is: 0.00011999999696854502 MOLE.Products are 0:C1CCN(C1)C2=CC3=C(C=C2)C=NN3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: _This reaction is done in triplicate_ : 6-bromo-1H-indazole (1.2 g, 6.09 mmol, 1 eq each), chloro(2-dicyclohexylphosphino-2',6'-di-i- propoxy-1,1'-biphenyl)[2-(2-aminoethylphenyl)]palladium(II), methyl-t- butylether adduct (RuPhos-PreCatalyst) (89 mg, 0.12 mmol, 0.02 eq each), 2-Dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl (RuPhos ligand) (57 mg, 0.12 mmol, 0.02 eq, each) were taken a stoppered bottle, flush with N2, pyrrolidine (0.60 ml, 522 mg. 7.34 mmol, 1.2 eq, each) and lithium bis(trimethylsilyl)amide (1M soln in THF, 15 ml, 15 mmol, 2.46 eq, each) were added in succession, flushed with N2, stoppered the bottle and stirred at 60 °C. LC-MS, after 2 hrs, showed that all the starting material is consumed. Cooled to r.t, queched the reaction with 2M HCl (9 ml, each), combined the reaction mixture and then extracted with EtOAc (250 ml) and saturated NaHCO3 (aq) soln. The organics was collected and the aq. layer was further extracted with EtOAc (250 ml). The combined organics was further washed with brine (250 ml). The organics was collected, dried (Na2SO4), filtered and evaporated to a brown solid (4.01 g, combined crude yield). The residue was chroamtographed (SiO2 - 100 g, Biotage-Pre-packed colum, heptane-EtOAC 5:1 to 2:1 gradiant. The appropriate fractions were combined and evaporated to a light brown solids (TLC: Rf = 15 mm/63 mm, heptane-EtOAc 1:1, _compound in TLC plate beome grey colored upon standing for few minutes_ ) corresponds to the required product (P1) (Starting material comes at 28 mm/63 mm in the same solvent system). _EN07765-42-01 (SN1050263564; AZ13824296-001_ ): 3.207 g (total yield, so each batch should be 1.069 g, 94%, ca 96% pure). 1H NMR (500 MHz, DMSO) d 1.94 - 2 (m, 4H), 3.27 (t, 4H), 6.34 (s, 1H), 6.56 (dd, 1H), 7.50 (d, 1H), 7.78 (s, 1H), 12.35 (s, 1H). Expected Number of Hs: 13. Assigned Hs: 13. LC-MS: ESI-MS m/z: [M+H]\+ 188.2. Rf = 1.59 min/4 min and 1.48 min/4 min in acidic (pH3) and basic (pH10) system repectively. TLC: Rf = 15 mm/64 mm (SiO2-glas plate, heptane-EtOAc 1:1 v/v, spots were detected by UV254 ( _spot became grey colored upon standing the plate at r.t_.) |
Here is a chemical reaction formula: Reactants are amine:CN1CCNCC1, amount is: 0.0006189999985508621 MOLE;aryl halide:CN1C(=NC(=N1)Br)Br, amount is: 0.0005890000029467046 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.001180000021122396 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.00017699999443721026 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 8.83999964571558e-05 MOLE.Products are 0:CN1CCN(CC1)C2=NC(=NN2C)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3,5-dibromo-1-methyl-1H-1,2,4-triazole (142 mg, 0.59 mmol), 1-methylpiperazine (62.0 mg, 0.62 mmol), tris(dibenzylideneacetone)dipalladium(0) (81 mg, 0.09 mmol), BINAP (110 mg, 0.18 mmol) and sodium tert-butoxide (113 mg, 1.18 mmol) in toluene (8 ml) was stirred at 100 °C for 1.5hrs. LCMS indicated no desired product formation. Discarded. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC(=C(N=C1)Br)Cl, amount is: 0.0020800000056624413 MOLE;amine:C1CC(C1)N, amount is: 0.0024900001008063555 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0036200000904500484 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 3.1200001103570685e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 1.5800000255694613e-05 MOLE.Products are 0:C1CC(C1)NC2=C(C=CC=N2)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Pd2(dba)3 (0.014 g, 0.02 mmol), 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (0.019 g, 0.03 mmol) and toluene (8 mL) was added to a flask. 2-bromo-3-chloropyridine (0.4 g, 2.08 mmol), cyclobutanamine (0.177 g, 2.49 mmol) and sodium 2-methylpropan-2-olate (0.348 g, 3.62 mmol) was added, the mixture bubbled with N2 for 5 min, then the reaction was heated to 115 °C in an oil-bath under nitrogen. LC-MS 1h: 33% product, 21% sm left. The reaction was cooled to rt and the solvent was evaporated. The residue was purified by automated flash chromatography on a 50g column. A gradient from 0% to 50% of EtOAc in heptane over 15CV was used as mobile phase. The product was collected using the wavelength 245 and 311 nm, relevant fractions pooled and evaporated to give 95 mg clear oil. 1H-NMR: OK, some extra small peaks in aromatic region (sm or dba?). 1H NMR (400 MHz, CDCl3) d 1.65 - 2.01 (m, 4H), 2.45 (dtd, 2H), 4.54 (h, 1H), 6.49 (dd, 1H), 7.41 (dd, 1H), 8.01 (dd, 1H). Expected Number of Hs: 11 Assigned Hs: 10, NH not assigned. LC-MS: OK, 86% product. M+1=183 found. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CN=CC=C1Br, amount is: 0.0063299997709691525 MOLE;amine:C1CNCC1O, amount is: 0.007600000128149986 MOLE,Reagents are Base:[Li+].C[Si](C)(C)[N-][Si](C)(C)C, amount is: 0.013899999670684338 MOLE,Solvents are Solvent:C1CCOC1, amount is: 0.0 ,Catalysts are metal and ligand:CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 0.0006329999887384474 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.0006329999887384474 MOLE.Products are 0:C1CN(CC1O)C2=CC=NC=C2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a 50 ml round bottomed flask THF (1 mL) was added to a mixture of 4-bromopyridine (1 g, 6.33 mmol), pyrrolidin-3-ol (0.662 g, 7.60 mmol),2-(dimethylamino)-2'-(dicyclohexylphosphino)biphenyl (0.249 g, 0.63 mmol) and Pd2(dba)3 (0.580 g, 0.63 mmol). To the slurry lithium bis(trimethylsilyl)amide (13.92 mL, 13.92 mmol) was added dropwise at 0 °C and the solution was refluxed at 65 °C overnight for 20 hrs. The reaction mixture was passed through celite, concentrated and column purified (0-20%MeOH/DCM) to obtain 0.447 mg of product. |
Here is a chemical reaction formula: Reactants are amine:C1C(CN1)(F)F.Cl, amount is: 0.0004780000017490238 MOLE;aryl halide:COC(=O)CC1=NC=CC(=C1)Br, amount is: 0.0004349999944679439 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0013000000035390258 MOLE,Solvents are Solvent:CN(C)C=O, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 4.349999926489545e-06 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 6.950000170036219e-06 MOLE.Products are 0:COC(=O)CC1=NC=CC(=C1)N2CC(C2)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: palladium acetate (1.561 mg, 6.95 µmol) and BINAP (2.71 mg, 4.35 µmol) were added to methyl 2-(4-bromopyridin-2-yl)acetate (100 mg, 0.43 mmol), 3,3 difluoroazetidine hydrochloride (61.9 mg, 0.48 mmol) and cesium carbonate (425 mg, 1.30 mmol) in DMF (5 mL) at 21°C under nitrogen. The resulting mixture was stirred at 120 °C for 2.5 hours. - lcms looks ok. Cooled to room temp.The reaction mixture was diluted with EtOAc (150 mL), and washed sequentially with water (75 mL), water (75 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 30 to 50% EtOAc in heptane. Pure fractions were evaporated to dryness - 200mg yellow oil. Contained Pd impurities. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 1M NH3/MeOH and pure fractions were evaporated to dryness to afford methyl 2-(4-(3,3-difluoroazetidin-1-yl)pyridin-2-yl)acetate (42.0 mg, 39.9 %) as a yellow gum. maybe better to avoid aq w/u and just purify by SCX column. |
Here is a chemical reaction formula: Reactants are aryl halide:CC(=O)C1=CC=C(C=C1)Br, amount is: 0.006029999814927578 MOLE;amine:CC(C)(C)OC(=O)N1CCNCC1, amount is: 0.009039999917149544 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.01209999993443489 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.00060299999313429 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00060299999313429 MOLE.Products are 0:CC(=O)C1=CC=C(C=C1)N2CCN(CC2)C(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a CEM MW vial, p-Bromoacetophenone (729 ml, 6.03 mmol),tert-Butyl 1-piperazinecarboxylate (1.684 g, 9.04 mmol),racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.375 g, 0.60 mmol),Palladium (II) acetate (0.135 g, 0.60 mmol),Cesium carbonate (3.93 g, 12.06 mmol) was taken in toluene (10 ml).The RM was subjected to MW power of 300W,temp 120°C for 45 minutes. The LCMS was checked showed the formation of required mass. Work-up: The RM was passed through hyflow bed and filtrate was evaporated and chrmatographed using Ethyl acetate hexane to obtain tert-butyl 4-(4-acetylphenyl)piperazine-1-carboxylate (0.963 g, 52.5 %). |
Here is a chemical reaction formula: Reactants are amine:CC1=CC(=C(C(=C1)C)S(=O)(=O)N[C@H](CN)C(C)C)C, amount is: 0.003010000102221966 MOLE;aryl halide:C1=CC2=C(C=NN2C3=CC=C(C=C3)F)C(=C1)Br, amount is: 0.003010000102221966 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.004509999882429838 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.0006939999875612557 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.00026199998683296144 MOLE.Products are 0:CC1=CC(=C(C(=C1)C)S(=O)(=O)N[C@H](CNC2=C3C=NN(C3=CC=C2)C4=CC=C(C=C4)F)C(C)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: BINAP (0.432 g, 0.69 mmol) and Pd2(dba)3 (0.24 g, 0.26 mmol) were dissolved in toluene (10 mL) and to this (S)-N-(1-amino-3-methylbutan-2-yl)-2,4,6-trimethylbenzenesulfonamide (0.856 g, 3.01 mmol) and 4-bromo-1-(4-fluorophenyl)-1H-indazole (0.876 g, 3.01 mmol) was added followed by sodium tert-butoxide (0.434 g, 4.51 mmol). The reaction mixture was degassed and the reaction tube was filled with nitrogen before it was heated at 110°C for 2h. LCMS indicated 55% product and just a small amout of starting materials remained. The reaction was partitioned between EtOAc and water. The layers were separated and the aqueous extracted twice with EtOAc. The organic extracts were combined, filtered through a fine sinter funnel to remove a grey ppte and then dried using a phase separator cartridge. The solvent was removed in vacuo and the residue purified by silica gel column chromatography (0-20% ethyl acetate in heptane). The product 340mg was obtained as a orange foam and was 90% clean by LCMS. The material was dissolved in DMSO and submitted to WRAP. (S)-N-(1-((1-(4-fluorophenyl)-1H-indazol-4-yl)amino)-3-methylbutan-2-yl)-2,4,6-trimethylbenzenesulfonamide (0.169 g, 11.38 %). Final form unknown. |
Here is a chemical reaction formula: Reactants are amine:CN1CCNCC1, amount is: 0.0022100000642240047 MOLE;aryl halide:CCOC(=O)C1=C(C2=CC(=C(C=C2N=C1)OC)Br)NC3=C(C=C(C=C3)Cl)Cl, amount is: 0.0014799999771639705 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.002950000111013651 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.00014800000644754618 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 7.380000170087442e-05 MOLE.Products are 0:CCOC(=O)C1=C(C2=CC(=C(C=C2N=C1)OC)N3CCN(CC3)C)NC4=C(C=C(C=C4)Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of ethyl 6-bromo-4-(2,4-dichlorophenylamino)-7-methoxyquinoline-3-carboxylate (694 mg, 1.48 mmol) and 1-methylpiperazine (0.246 mL, 2.21 mmol) in dioxane (10 mL) was added cesium carbonate (962 mg, 2.95 mmol), tris(dibenzylideneacetone)dipalladium(0) (67.6 mg, 0.07 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (92 mg, 0.15 mmol). Reaction vessel in oil bath set to 100 °C. 2.15pm o/n 20 hours - LCMS shows product (489) and SM (470) 26 hours - ratio of product : SM looks better by MS. 2 x o/n - small SM peak remaining in MS. Concentrated onto silica and purified on ISCO. 40g column, 4:1 H:EA, then gradient up to ~1:1 EA:MeOH. Can't find product by LCMS in any fractions. NMR of polar fractions may be acid from Buchwald coupling. Need to purify SM on column, repeat. |
Here is a chemical reaction formula: Reactants are amine:CC(C)(C)OC(=O)N1CCC[C@H](C1)N, amount is: 0.04800000041723251 MOLE;aryl halide:CC1=C(N=CC=C1)Br, amount is: 0.040300000458955765 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0016899999463930726 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.0016899999463930726 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.0007779999868944287 MOLE.Products are 0:CC1=C(N=CC=C1)N[C@@H]2CCCN(C2)C(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Production using the conditions which were shown to work in EN07957-76 2016-03-01 14:20; Pd2(DBA)3 (1.05 g) and BINAP (712 mg mg) was stirred in toluene (75 ml). 14:25; 2-bromo-3-methylpyridine (6.94 g), the amine (9.62 g), and sodium t-butoxide (5.43 g), was added to the mixture. 14:30; Heating at 115 °C. In an attempt to degas the reaction by employing vacuum to the flask good reflux, indicating a slight exotherm, took place. HPLC after 5 minutes indicated complet reaction. The mixture was allowed to cool. 2016-03-02 09:00; Water (50 ml) was followowed by 0.5 M citric acid (~75 ml) to give pH 3. The aqueous phase was extracted with another 25 ml toluene and the combined extracts were washed with water. Removal of the solvent in vacuo followed by evaporation of the solvent gave a reddish brown residue, 13.3 g. The mixture was dissolved in toluene and purified on a 100 g silica column, 25-100% ethyl acetate over 6 columns, collecting at 300 nm. This flash was repeated on a 340 g silica column to give 6.24 g oil with a clear orange color. About 4 g more impure material was also isolated. It was realized that preparative HPLC was required for purifiaction of the material. The impurity was mainly the diphosphine oxide originating from the BINAP. All material was purifed by preparative HPLC, 15-65% ACN in TFA 0.1%. The eluents were neutralized with ammonia and the acetonitrile was removed in vacuo. Extraction with DCM, drying (magnesium sulfate) and removal of the solvent in vacuo (over the weekend) gave 8.21 g semicrystalline material. The 1H-NMR and 13C NMR looks slightly dubious (too many protons and a13C shift at 3.8 ppm) but probably good enough for further synthesis. |
Here is a chemical reaction formula: Reactants are aryl halide:CC1=C(N=CC=C1)Br, amount is: 0.0020000000949949026 MOLE;amine:CC(C)(C)OC(=O)N1CCC[C@H](C1)N, amount is: 0.002630000002682209 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 3.0499999411404133e-05 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 3.0499999411404133e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 1.5300000086426735e-05 MOLE.Products are 0:CC1=C(N=CC=C1)N[C@@H]2CCCN(C2)C(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Test reaction using the conditions which were shown to work in EN07957-76 2016-02-26 14:30; Pd2(DBA)3 (14 mg) and BINAP (19 mg) was stirred in toluene (2.5 ml). 14:35; 2-bromo-3-methylpyridine (344 mg), sodium t-butoxide (334 mg), and the amine (526 mg) was added to the mixture. 14:40; Heating at 115 °C. 15:10; 81% product. 15:40; 81% product, No further progress was observed, probably because of lack of amine 15:50; Another 0.4 ml amine was added to the mixture. 16:15; No further progress by HPLC, reaction terminated. 50 microlitres of the mixture was evaporated and the residue was dissolved in methanol-d4 and 1H NMR was recorded. By 1H NMR the starting pyridine was consumed completely, as opposed to the HPLC-MS which indicated 16% starting material. 2016-02-29 10:35; Purification using 25-100% ethyl acetate in heptane over 6 column lengths on a 50 g column, detection at 300 nm and collection on threshold 50 mAU. Evaporation fo the fractions gave 480 mg oil. ee measurement showed 99.9% ee |
Here is a chemical reaction formula: Reactants are aryl halide:CCOC(=O)C1=CN=C2C=CC(=CC2=C1NC3=C(C=C(C=C3)F)F)Br.Cl, amount is: 0.0011399999493733048 MOLE;amine:CN1CCNCC1, amount is: 0.0017099999822676182 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0034099998883903027 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.0001140000022132881 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 5.690000034519471e-05 MOLE.Products are 0:CCOC(=O)C1=CN=C2C=CC(=CC2=C1NC3=C(C=C(C=C3)F)F)N4CCN(CC4)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of ethyl 6-bromo-4-(2,4-difluorophenylamino)quinoline-3-carboxylate hydrochloride (505 mg, 1.14 mmol) and 1-methylpiperazine (0.189 mL, 1.71 mmol) in dioxane (10 mL) was added cesium carbonate (1113 mg, 3.41 mmol), tris(dibenzylideneacetone)dipalladium(0) (52.1 mg, 0.06 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (70.9 mg, 0.11 mmol). Reaction vessel in oil bath set to 100 °C. 3pm o/n - 20 hours, LCMS shows mostly SM (408), trace of product (427). Heating stopped after 24 hours. 8/6/08 - Additional portions of Pd cat, BINAP and Me piperazine added, and reaction returned to oil bath at 105C. o/n - Reaction more advanced, but still mostly SM. From past experience, Buchwald coupling may be more successful if SM is purified on silica column first. Discarded |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC2=C(C(=C1)Br)NC=C2, amount is: 0.001610000035725534 MOLE;amine:CC(C)(C)OC(=O)N1CCNCC1, amount is: 0.001610000035725534 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.002420000033453107 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 0.0001610000035725534 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 8.05000017862767e-05 MOLE.Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2NC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl (75 mg, 0.16 mmol) and palladium (II) acetate (18.08 mg, 0.08 mmol) were dissoved in toluene (2 mL) at ambient temperature. The mixture was degassed and purged with nitrogen and warmed to 50°C for 20 mins. In a separate vessel, were mixed tert-butyl piperazine-1-carboxylate (300 mg, 1.61 mmol), 7-bromo-1H-indole (316 mg, 1.61 mmol) and sodium-t-butoxide (296 mL, 2.42 mmol) in toluene (3 mL). The mixture was degasssed and purged with nitrogen and warmed to 50°C. The catalyst solution was added to the reaction vessel and the resulting mixture was degassed and purged with nitrogen and heated at 100°C for overnight. UPLC analysis showed virtually no reaction (only 7% conversion to product). Reaction abandoned. |
Here is a chemical reaction formula: Reactants are aryl halide:COC1=CC=CC=C1Br, amount is: 0.0032099999953061342 MOLE;amine:CC(C)(C)OC(=O)N1CCNCC1, amount is: 0.0032099999953061342 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0051299999468028545 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.00012799999967683107 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 6.420000136131421e-05 MOLE.Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC=C2OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.059 g, 0.06 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.080 g, 0.13 mmol) were mixed in toluene (10 mL) and degessed at 90 °C for 10 mins. The mixture was then cooled and 1-bromo-2-methoxybenzene (0.400 mL, 3.21 mmol), sodium 2-methylpropan-2-olate (0.493 g, 5.13 mmol) and tert-butyl piperazine-1-carboxylate (0.597 g, 3.21 mmol) were added. The resulting mixture was stirred at 100 °C for 16 hours under nitrogen. The reaction mixture was filtered through celite and the filtrate concentrated. The crude product was purified by flash silica chromatography, elution gradient 20 to 100% EtOAc in heptane. Pure fractions were evaporated to dryness to afford tert-butyl 4-(2-methoxyphenyl)piperazine-1-carboxylate (0.585 g, 62.4 %) as a yellow oil which crystallised on standing. |
Here is a chemical reaction formula: Reactants are amine:CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)N, amount is: 0.004290000069886446 MOLE;aryl halide:CC1(CCN2C(=C(C=N2)C3=CC(=NC=C3F)Cl)C1)C, amount is: 0.004290000069886446 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.012900000438094139 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0008580000139772892 MOLE;metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd], amount is: 0.0004290000069886446 MOLE.Products are 0:CC1(CCN2C(=C(C=N2)C3=CC(=NC=C3F)NC(=O)[C@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Tetrakis(triphenylphosphine)palladium(0) (0.496 g, 0.43 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-5,5-dimethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine (1.2g, 4.29 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (1.039 g, 4.29 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.496 g, 0.86 mmol) and Cesium carbonate (4.19 g, 12.87 mmol) in 1,4-dioxane (10 mL)Degassed for 5 mins under nitrogen and the resulting suspension was stirred at 120 °C for 17 hours in the microwave reactor. The reaction mixture was partitioned between water (20ml) and ethyl acetate (100ml) filtered and separated. The organics were absorbed onto silica and purified by flash silica chromatography, elution gradient 1:1 EtOAc in heptane. Pure fractions were evaporated to dryness to afford tert-butyl ((1R,3S)-3-((4-(5,5-dimethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl)-5-fluoropyridin-2-yl)carbamoyl)cyclohexyl)carbamate (1.100 g, 52.8 %) as a white solid. |
Here is a chemical reaction formula: Reactants are amine:CS(=O)(=O)CC1=CC(=CC(=C1)F)N, amount is: 0.00046800001291558146 MOLE;aryl halide:COC1=C(C=CC(=C1)F)C2=NC(=NC=C2F)Cl, amount is: 0.00046800001291558146 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.00011700000322889537 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.00011700000322889537 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 9.349999891128391e-05 MOLE.Products are 0:COC1=C(C=CC(=C1)F)C2=NC(=NC=C2F)NC3=CC(=CC(=C3)CS(=O)(=O)C)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-chloro-5-fluoro-4-(4-fluoro-2-methoxyphenyl)pyrimidine (0.12 g, 0.47 mmol), 3-fluoro-5-((methylsulfonyl)methyl)aniline (0.095 g, 0.47 mmol), cesium carbonate (0.609 g, 1.87 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.068 g, 0.12 mmol)and Pd2(dba)3 (0.086 g, 0.09 mmol) were suspended in degassed 1,4-dioxane (3 mL) at ambient temperature. The resulting mixture was degassed, purged with nitrogen and heated at 100 °C for 3 hours after which time reaction was shown to be complete by LC-MS. The mixture was allowed to cool overnight. The reaction mixture was diluted with water (250 mL), and extracted with DCM (250 mL). The organic was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution 50% ethyl acetate in Heptane. Fractions were evaporated to dryness to afford crude product. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5µ silica, 50 mm diameter, 150 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 5-fluoro-4-(4-fluoro-2-methoxyphenyl)-N-(3-fluoro-5-((methylsulfonyl)methyl)phenyl)pyrimidin-2-amine (0.120 g, 60.6 %) as a white solid. |
Here is a chemical reaction formula: Reactants are aryl halide:CC1(CC2=C(C=NN2C1)C3=CC(=NC=C3F)Cl)C, amount is: 0.0004889999981969595 MOLE;amine:CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)N, amount is: 0.0004889999981969595 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0014700000174343586 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 9.780000254977494e-05 MOLE;metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd], amount is: 4.890000127488747e-05 MOLE.Products are 0:CC1(CC2=C(C=NN2C1)C3=CC(=NC=C3F)NC(=O)[C@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Tetrakis(triphenylphosphine)palladium(0) (56.5 mg, 0.05 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (130 mg, 0.49 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (119 mg, 0.49 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (56.6 mg, 0.10 mmol) and Cesium carbonate (478 mg, 1.47 mmol) in 1,4-dioxane (5.98 ml). Degassed for 5 mins under nitrogen and the resulting suspension was stirred at 120 °C for 2 hours in the microwave reactor. The reaction mixture was partitioned between water (20ml) and DCM (40ml) and separated using a phase separation cartridge. The organics were absorbed onto silica and purified by flash silica chromatography, elution gradient 0 to 60% EtOAc in heptane. Pure fractions were evaporated to dryness to afford tert-butyl ((1R,3S)-3-((4-(5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-5-fluoropyridin-2-yl)carbamoyl)cyclohexyl)carbamate (81 mg, 35.1 %) as a pale yellow solid. |
Here is a chemical reaction formula: Reactants are amine:CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)N, amount is: 0.0013800000306218863 MOLE;aryl halide:CC1(CC2=C(C=NN2C1)C3=CC(=NC=C3F)Cl)C, amount is: 0.0013800000306218863 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.004129999782890081 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0002749999985098839 MOLE;metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd], amount is: 0.00013800000306218863 MOLE.Products are 0:CC1(CC2=C(C=NN2C1)C3=CC(=NC=C3F)NC(=O)[C@H]4CCC[C@H](C4)NC(=O)OC(C)(C)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Tetrakis(triphenylphosphine)palladium(0) (159 mg, 0.14 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (365.4 mg, 1.38 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (333 mg, 1.38 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (Xantphos) (159 mg, 0.28 mmol)and Cesium carbonate (1344 mg, 4.13 mmol) in 1,4-dioxane (15 mL). The resulting suspension was degassed for 10 minutes under nitrogen and then stirred at 120 °C for 8 hours overnight in the microwave reactor. The reaction mixture was partioned between water (30 mL) and DCM (15 mL) and seperated. _LCMS analysis showed product in the aqueous extract._ The aqueous layer was extracted with DCM (2 X 20 mL). LCMS analysis showed some product still within in the aqueous extract. _The aqueous layer was extracted again with DCM (2 X 25 mL). _ The organic extracts were combined, dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 60% EtOAc in heptane. Pure fractions were evaporated to dryness to afford tert-butyl ((1R,3S)-3-((4-(5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-5-fluoropyridin-2-yl)carbamoyl)cyclohexyl)carbamate (348 mg, 53.6 %) as a white solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC=C(C=C1)Br, amount is: 0.0005680000176653266 MOLE;amine:C1CCNC(C1)C2=CC=CC=C2, amount is: 0.0006820000126026571 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0017099999822676182 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 2.8399999791872688e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 1.4199999895936344e-05 MOLE.Products are 0:C1CCN(C(C1)C2=CC=CC=C2)C3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Caesium carbonate (556 mg, 1.71 mmol) was added to bromobenzene (0.060 mL, 0.57 mmol) and 2-phenylpiperidine (110 mg, 0.68 mmol) in 1,4-dioxane (2 mL). The reaction was degassed and Tris(dibenzylideneacetone)?dipalladium(0) (13.01 mg, 0.01 mmol) and dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (RuPhos) (13.26 mg, 0.03 mmol) were added. The resulting solution was stirred at 100 °C for 16 hours. LCMS showed The reaction mixture was diluted with EtOAc, and washed with water. The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 15% MeOH in DCM. Pure fractions were evaporated to dryness to afford 1,2-diphenylpiperidine (21.00 mg, 15.56 %) as a yellow oil. f0 = 19 mg bromobenzene f1 = 21 mg product The reaction was abandonned. |
Here is a chemical reaction formula: Reactants are amine:CC(C)(C)OC(=O)N1CCNCC1, amount is: 0.0034099998883903027 MOLE;aryl halide:COC1=C(C=CC(=C1)Br)OCC2=CC=CC=C2, amount is: 0.0034099998883903027 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.004780000075697899 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.00013600000238511711 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.00010199999815085903 MOLE.Products are 0:COC1=C(C=CC(=C1)N2CCNCC2)OCC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To tert-butyl piperazine-1-carboxylate (0.635 g, 3.41 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.094 g, 0.10 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.085 g, 0.14 mmol) and Sodium tert-butoxide (0.459 g, 4.78 mmol) was added a solution of 1-(benzyloxy)-4-bromo-2-methoxybenzene (1 g, 3.41 mmol) in Toluene (25 mL). The resulting solution was stirred at reflux for18 hours. The reaction was allowed to cool to room temperature and diluted with dcm (50 ml). This was washed with water (2 x 50 ml), dried over sodium sulfate, filtered and the solvent removed under reduced pressure. The crude product was dissolved in hydrochloric acid solution in methanol (4N, 20 ml) and stirred at room temprature overnight. The solvent was removed under reduced pressure.The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and pure fractions were evaporated to dryness to afford 1-(4-(benzyloxy)-3-methoxyphenyl)piperazine (0.614 g, 60.3 %) as a yellow gum. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CN=CC=C1Br, amount is: 0.03610000014305115 MOLE;amine:C1=CC=C(C=C1)N, amount is: 0.043299999088048935 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.05050000175833702 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.00215999991632998 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0007220000261440873 MOLE.Products are 0:C1=CC=C(C=C1)NC2=CC=NC=C2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: ANILINE (3.94 mL, 43.29 mmol) was added to 4-bromopyridine (5.7 g, 36.08 mmol), PALLADIUM(II) ACETATE (0.162 g, 0.72 mmol), XANTPHOS (1.252 g, 2.16 mmol) and SODIUM TERT-BUTOXIDE (4.85 g, 50.51 mmol) in toluene (280 mL) under nitrogen. The resulting mixture was stirred at 100 °C for 4 hours. The reaction mixture was evaporated to dryness and redissolved in EtOAc (200 mL), and washed sequentially with water (2 x 100 mL) and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and preadsorbed onto silica. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in heptane. Pure fractions were evaporated to dryness to afford N-phenylpyridin-4-amine (1.528 g, 24.88 %) as a pink solid. |
Here is a chemical reaction formula: Reactants are amine:C1=CC=C(C=C1)N, amount is: 0.01899999938905239 MOLE;aryl halide:C1=CN=CC=C1Br, amount is: 0.015799999237060547 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.022199999541044235 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.0009490000084042549 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00031599999056197703 MOLE.Products are 0:C1=CC=C(C=C1)NC2=CC=NC=C2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: ANILINE (1.730 mL, 18.99 mmol) was added to 4-bromopyridine (2.5 g, 15.82 mmol), PALLADIUM(II) ACETATE (0.071 g, 0.32 mmol), XANTPHOS (0.549 g, 0.95 mmol) and SODIUM TERT-BUTOXIDE (2.129 g, 22.15 mmol) in toluene (125 mL) under nitrogen. The resulting mixture was stirred at 100 °C for 4 hours. The reaction mixture was evaporated to dryness and redissolved in EtOAc (100 mL), and washed sequentially with water (2 x 100 mL) and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and preadsorbed onto silica. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in heptane. Pure fractions were evaporated to dryness to afford N-phenylpyridin-4-amine (1.102 g, 40.9 %) as a white solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CN=CC=C1Br, amount is: 0.06270000338554382 MOLE;amine:C1=CC=C(C=C1)N, amount is: 0.07519999891519547 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0877000018954277 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.003759999992325902 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0012499999720603228 MOLE.Products are 0:C1=CC=C(C=C1)NC2=CC=NC=C2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: ANILINE (6.85 mL, 75.19 mmol) was added to 4-bromopyridine (9.9 g, 62.66 mmol), PALLADIUM(II) ACETATE (0.281 g, 1.25 mmol), XANTPHOS (2.175 g, 3.76 mmol) and SODIUM TERT-BUTOXIDE (8.43 g, 87.72 mmol) in toluene (500 mL) under nitrogen. The resulting mixture was stirred at 100 °C for 4 hours. The reaction mixture was evaporated to dryness and redissolved in EtOAc (200 mL), and washed sequentially with water (2 x 100 mL) and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and preadsorbed onto silica. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in heptane. Pure fractions were evaporated to dryness to afford N-phenylpyridin-4-amine (2.160 g, 20.25 %) as a pale tan solid. |
Here is a chemical reaction formula: Reactants are aryl halide:CC(C)(C)OC(=O)N1C=CC2=C1C(=CC=C2)Br, amount is: 0.0016899999463930726 MOLE;amine:CC(C)(C)OC(=O)N1CCNCC1, amount is: 0.0016899999463930726 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.002529999939724803 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 0.0003380000125616789 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00016900000628083944 MOLE.Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2N(C=C3)C(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Palladium (II) acetate (37.9 mg, 0.17 mmol) and 2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl (158 mg, 0.34 mmol) were dissolved in toluene (3 mL) and the resulting solution degassed and purged with nitrogen. The mixture was warmed to 50°C for 15 mins. In a separate vessel, were mixed tert-butyl piperazine-1-carboxylate (314 mg, 1.69 mmol), tert-butyl 7-bromo-1H-indole-1-carboxylate (500 mg, 1.69 mmol) and sodium-t-butoxide (243 mg, 2.53 mmol) in toluene at ambient temperature. The mixture was degassed and purged with nitrogen. The catalyst solution was added and the resulting mixture heated at 100°C under nitrogen overnight. The main product of the reaction is 7-bromoindole. Boc has been lost (high temp, base). Only small trace desired product visible in UPLC. Reaction abandoned. Try lower temps, different base? |
Here is a chemical reaction formula: Reactants are amine:CC(C)(C)OC(=O)N1CCNCC1, amount is: 0.0003380000125616789 MOLE;aryl halide:CC(C)(C)OC(=O)N1C=CC2=C1C(=CC=C2)Br, amount is: 0.0003380000125616789 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.000506000011228025 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 6.749999738531187e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.3799999073380604e-05 MOLE.Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC3=C2N(C=C3)C(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: _Trial reaction_ Palladium (II) acetate (7.58 mg, 0.03 mmol) and 2-Dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl (31.5 mg, 0.07 mmol) were suspended in 1,4-dioxane (1 mL) at ambient temperature. The mixture was degassed and purged with nitrogen and warmed to 50°C for 20 mins. In a separate vessel, were mixed tert-butyl piperazine-1-carboxylate (62.9 mg, 0.34 mmol), tert-butyl 7-bromo-1H-indole-1-carboxylate (100 mg, 0.34 mmol) and cesium carbonate (165 mg, 0.51 mmol) in 1,4-dioxane (2 mL). The mixture was degassed and purged with nitrogen several times. The catalyst solution was added and the resulting mixture was heated at 95°C overnight under a nitrogen atmosphere. No reaction observed by LCMS. Main component of the mixture was unreacted BOC- protected indole. No loss of BOC, but still no reaction. |
Here is a chemical reaction formula: Reactants are amine:C1=COC(=N1)N, amount is: 0.0012000000569969416 MOLE;aryl halide:C1=CC=NC(=C1)Cl, amount is: 0.0010000000474974513 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.00139999995008111 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 2.9999999242136255e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 1.9999999494757503e-05 MOLE.Products are 0:C1=CC=NC(=C1)NC2=NC=CO2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Palladium(II) acetate (4.49 mg, 0.02 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.017 g, 0.03 mmol) were mixed together in a reaction vessel and evacuated and purged with nitrogen 3 times. Dioxane (1 mL) was added and the resulting mixture was heated to to 50°C for 30 minutes. oxazol-2-amine (0.101 g, 1.20 mmol) together with 2-chloropyridine (0.094 mL, 1.00 mmol) and cesium carbonate (0.456 g, 1.40 mmol) were placed in a second vessel, evacuated and purged with nitrogen 3 times and dioxane (3 mL) was added. The catalyst solution was added and the resulting mixture heated at 100 °C for 16 hours. **No oxazol-2-amine present in proton NMR of crude reaction mixture.** The starting material is decomposing under the reaction conditions, could be the route of the very low productivity in the C-N couplings using these substrates. Only chloropyridine observed in the proton NMR and LCMS of the crude reaction mixture. Conclusion: Experiment abandoned, none of the desired product isolated. . |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC=NC(=C1)Cl, amount is: 0.0010000000474974513 MOLE;amine:C1=COC(=N1)N, amount is: 0.0020000000949949026 MOLE,Reagents are Base:C(=O)([O-])[O-].[K+].[K+], amount is: 9.999999747378752e-05 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)(C)P(C1=CC2=CC=CC=C2N1C3=CC=CC=C3)C(C)(C)C, amount is: 0.00019999999494757503 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 4.999999873689376e-05 MOLE.Products are 0:C1=CC=NC(=C1)NC2=NC=CO2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Objective: Comparison of the reactivity of 2-aminooxazole in the coupling with 2-chloropyridine using three different catalyst systems ( previously shown to be the best performers in a 96-well Process Research and Development Screen) To an oven-dried microwave vial was added TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.046 g, 0.05 mmol) and 2-(di-tert- butylphosphino)-1-phenyl-1H-indole (0.067 g, 0.2 mmol) and the vial was purged with nitrogen. dioxane (2 mL) (degassed) was added and the reaction mixture was heated to 50 °C for 40 min followed by heating to 90 °C for a further 15 min (Solution 1). To an oven dried microwave vial was added 2-chloropyridine (0.095 mL, 1 mmol), oxazol-2-amine (0.187 g, 2.00 mmol), potassium carbonate (0.207 g, 1.50 mmol) and 4,4'-di-tert-butylbiphenyl (0.027 g, 0.1 mmol). The vial was then capped and purged with nitrogen. To this was added the activated catalyst solution (Solution 1) . The reaction mixture was then heated to 90 °C for 16 h under an inert atmosphere. LCMS of the crude reaction mixture under basic conditions showed a peak which had the mass of the desired product, however, the chloropyridine starting material co-elutes under these conditions. Under acidic conditions none of the desired product mass was observed at Rt= 0.25 min (whereas for EN05378-80 and EN05378-81, the product mass was observed at this retention time). A product of mass corresponding to homo-coupled product was observed under basic conditions. Reaction not progressed. Conclusion: The 't-Butyl Beller ligand' was not efficent for the coupling of these substrates under the above conditions. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC=NC(=C1)Cl, amount is: 0.0010000000474974513 MOLE;amine:C1=COC(=N1)N, amount is: 0.0020000000949949026 MOLE,Reagents are Base:C(=O)([O-])[O-].[K+].[K+], amount is: 9.999999747378752e-05 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=C(C=CC(=C2P(C3CCCCC3)C4CCCCC4)OC)OC)C(C)C, amount is: 0.00019999999494757503 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 4.999999873689376e-05 MOLE.Products are 0:C1=CC=NC(=C1)NC2=NC=CO2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Objective: Comparison of the reactivity of 2-aminooxazole in the coupling with 2-chloropyridine using three different catalyst systems ( previously shown to be the best performers in a 96-well Process Research and Development Screen) To an oven-dried microwave vial was added TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.046 g, 0.05 mmol) and dicyclohexyl(2',4',6'-triisopropyl-3,6-dimethoxybiphenyl-2-yl)phosphine (0.107 g, 0.2 mmol) and the vial was capped and purged with nitrogen. dioxane (2 mL) (degassed) was added and the reaction [Reactants]mixture was heated to 50 °C for 40 min followed by heating to 90 °C for a further 15 min (Solution 1). To an oven dried microwave vial was added 2-chloropyridine (0.095 mL, 1 mmol), oxazol-2-amine (0.187 g, 2.00 mmol), potassium carbonate (0.207 g, 1.50 mmol) and 4,4'-di-tert-butylbiphenyl (0.027 g, 0.1 mmol). The vial was then capped and purged with nitrogen. To this was added the activated catalyst solution (Solution 1). The reaction mixture was then heated to 90 °C for 16 h under an inert atmosphere. LCMS of the crude reaction mixture (Base) showed the mass peak for the desired product, however, this peak co-elutes with the Cl-pyridine starting material. LCMS of the crude reaction mixture using an acidic method showed no peak in the UV which had a mass corresponding to that of the product, however, the desired mass was observed in the MS at Rt= 0.27 min. A peak in the UV of a mass corresponding to the homocoupled bipyridine product was observed under both acidic and basic methods. Dichloromethane was added to the crude reaction mixture together with silica (2 g). The solvent was removed under reduced pressure and the resulting residue was placed in a dry-load tube prior to chromatography. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% methanolic ammonia (7 M) in DCM. 2-aminooxazole (103 mg) was recovered. The fraction containing the mass of the desired product produced 33 mg of impure material (see attached proton NMR, the desired product **_may_** be present (but it's hard to say). If this sample was to be pure it would correspond to an isolated yield of ~ 20% of the desired product, due to the fact that this is a really impure sample the real value is probably less than 10%. Conclusion: Reaction not progressed. |
Here is a chemical reaction formula: Reactants are amine:C1COCCN1, amount is: 0.10000000149011612 MOLE;aryl halide:C1=CNC2=NC=C(C=C21)Br, amount is: 0.050200000405311584 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.10000000149011612 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 0.0025100000202655792 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0050200000405311584 MOLE.Products are 0:C1COCCN1C2=CN=C3C(=C2)C=CN3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine (9.9 g, 50.25 mmol), morpholine (7.96 mL, 100.49 mmol), sodium 2-methylpropan-2-olate (19.32 g, 200.98 mmol),dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (1.172 g, 2.51 mmol) in degassed dioxane (200 mL) was added diacetoxypalladium (1.128 g, 5.02 mmol) and the reaction mixture was heated under nitrogen at 90 °C for 17 hours, then evaporated and partitioned between DCM (150 ml) and saturated aqueous sodium bicarbonate solution (150 mL). The aqueous phase was extracted further with DCM (70 ml) and the combined organics were evaporated, redissolved in a mixture of methanol and DCM and purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford 4-(1H-pyrrolo[2,3-b]pyridin-5-yl)morpholine (8.54 g, 84 %) as a yellow solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CNC2=NC=C(C=C21)Br, amount is: 0.02590000070631504 MOLE;amine:C1COCCN1, amount is: 0.05180000141263008 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.05180000141263008 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 0.001290000043809414 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.002589999930933118 MOLE.Products are 0:C1COCCN1C2=CN=C3C(=C2)C=CN3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine (5.1 g, 25.88 mmol), morpholine (4.10 mL, 51.77 mmol), sodium 2-methylpropan-2-olate (9.95 g, 103.54 mmol),dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (0.604 g, 1.29 mmol) in degassed dioxane (100 mL) was added diacetoxypalladium (0.581 g, 2.59 mmol) and the reaction mixture was heated under nitrogen at 90 °C for 17 hours, then evaporated and partitioned between DCM (80ml) and saturated aqueous sodium bicarbonate solution (80ml). The aqueous phase was extracted further with DCM (50ml) and the combined organics were evaporated, redissolved in a mixture of methanol and DCM and purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford 4-(1H-pyrrolo[2,3-b]pyridin-5-yl)morpholine (3.40 g, 64.6 %) as a yellow solid. |
Here is a chemical reaction formula: Reactants are amine:C1COCCN1, amount is: 0.10000000149011612 MOLE;aryl halide:C1=CNC2=NC=C(C=C21)Br, amount is: 0.050200000405311584 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.10000000149011612 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 0.0050200000405311584 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0025100000202655792 MOLE.Products are 0:C1COCCN1C2=CN=C3C(=C2)C=CN3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine (9.9 g, 50.25 mmol), morpholine (7.96 mL, 100.49 mmol), sodium 2-methylpropan-2-olate (19.32 g, 200.98 mmol),dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (2.345 g, 5.02 mmol) in degassed dioxane (200 mL) was added diacetoxypalladium (0.564 g, 2.51 mmol) and the reaction mixture was heated under nitrogen at 90 °C for 17 hours, then evaporated and partitioned between DCM (150 mL) and saturated aqueous sodium bicarbonate solution (150 mL). The aqueous phase was extracted further with DCM (70 mL) and the combined organics were concentrated. The crude material was purified by flash silica chromatography, elution gradient 0 to 5% MeOH in DCM. Pure fractions were evaporated to dryness to afford 4-(1H-pyrrolo[2,3-b]pyridin-5-yl)morpholine (9.28 g, 91 %) as a yellow solid. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F, amount is: 0.017799999564886093 MOLE;amine:CC(C)(C)[Si](C)(C)OCCN, amount is: 0.017799999564886093 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0017800000496208668 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C, amount is: 0.0017800000496208668 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0017800000496208668 MOLE.Products are 0:CC(C)(C)[Si](C)(C)OCCNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: PdOAc2 (0.399 g, 1.78 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.848 g, 1.78 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (5.00 g, 17.79 mmol), 2-(tert- butyldimethylsilyloxy)ethanamine (4.16 g, 17.79 mmol) and cesium carbonate (8.69 g, 26.68 mmol) in toluene (100 mL) at 20°C in a microwave vial. The microwave vial was sealed and the reaction was heated to 120 °C for 10 hours in the microwave reactor and cooled to RT. **** _Split into 5 x 20 ml mw vials such as in each was:_ PdOAc2 (0.080 g, 0.36 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.170 g, 0.36 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (1.000 g, 3.56 mmol), 2-(tert- butyldimethylsilyloxy)ethanamine (0.832 g, 3.56 mmol) and cesium carbonate (1.739 g, 5.34 mmol) in toluene (20 mL) at 20°C in a microwave vial. The microwave vial was sealed and the reaction was heated to 120 °C for 10 hours in the microwave reactor and cooled to RT. **** The reaction mixtures were combined and diluted with EtOAc (150 mL), and washed sequentially with water (200 mL) and saturated brine (200 mL). The organic layer was filtered and dried over Na2SO4, filtered and evaporated to afford crude product. The crude product was evaporated and was purified by flash silica chromatography, elution gradient 0 to 30% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 4-(benzyloxy)-N-(2-(tert- butyldimethylsilyloxy)ethyl)-3-fluoroaniline (3.62 g, 54.2 %) as a yellow oil. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC=C(C=C1)COC2=C(C=C(C=C2)Br)F, amount is: 0.0018899999558925629 MOLE;amine:CC(C)(C)[Si](C)(C)OCCN, amount is: 0.0018899999558925629 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.00018899999849963933 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C, amount is: 0.00018899999849963933 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00018899999849963933 MOLE.Products are 0:CC(C)(C)[Si](C)(C)OCCNC1=CC(=C(C=C1)OCC2=CC=CC=C2)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: PdOAc2 (42.3 mg, 0.19 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (90 mg, 0.19 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (530 mg, 1.89 mmol), 2-(tert- butyldimethylsilyloxy)ethanamine (441 mg, 1.89 mmol) and cesium carbonate (921 mg, 2.83 mmol) in toluene (15 mL) at 20°C in a microwave vial. The microwave vial was sealed and the reaction was heated to 120 °C for 12 hours in the microwave reactor and cooled to RT. The reaction mixture was diluted with EtOAc (50 mL), and washed sequentially with water (50 mL) and saturated brine (50 mL). The organic layer was filtered and dried over Na2SO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 30% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 4-(benzyloxy)-N-(2-(tert- butyldimethylsilyloxy)ethyl)-3-fluoroaniline (312 mg, 44.1 %) as a yellow oil. |
Here is a chemical reaction formula: Reactants are amine:CNC1=CC=C(C=C1)F, amount is: 0.0027799999807029963 MOLE;aryl halide:COC(=O)C1=CC(=NC=C1)Br, amount is: 0.002309999894350767 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0032399999909102917 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4, amount is: 0.00034699999378062785 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.00011600000289035961 MOLE.Products are 0:CN(C1=CC=C(C=C1)F)C2=NC=CC(=C2)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a 100 mL round-bottomed flask (t=g) was methyl 2-bromoisonicotinate (.5 g, 2.31 mmol), 4-fluoro-N-methylaniline (0.348 g, 2.78 mmol), and CS2CO3 (1.056 g, 3.24 mmol) in toluene (16 mL) to give a yellow suspension. Pd2dba3 (0.106 g, 0.12 mmol) and biphenyl-2-yldicyclohexylphosphine (0.122 g, 0.35 mmol) were added. Reaction was allowed to stir overnight. LC/MS in the morning revealed little product had formed. Something with mass 272 dominated. Reaction was discarded. |
Here is a chemical reaction formula: Reactants are amine:CNC1=CC=C(C=C1)F, amount is: 0.0005549999768845737 MOLE;aryl halide:COC(=O)C1=CC(=NC=C1)Br, amount is: 0.00046300000394694507 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0006479999865405262 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4, amount is: 6.939999730093405e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 2.3099999452824704e-05 MOLE.Products are 0:CN(C1=CC=C(C=C1)F)C2=NC=CC(=C2)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a 100 mL round-bottomed flask (t=g) was biphenyl-2-yldicyclohexylphosphine (0.024 g, 0.07 mmol), methyl 2-bromoisonicotinate (.1 g, 0.46 mmol), and 4-fluoro-N-methylaniline (0.070 g, 0.56 mmol) in toluene (3 mL) to give a purple suspension. Pd2dba3 (0.021 g, 0.02 mmol) and CS2CO3 (0.211 g, 0.65 mmol) were added. Flask was placed in an oil bath at 85 °C. LC/MS taken at 1, 2 and 4 hours indicated reaction was not progressing. Reaction was discarded. |
Here is a chemical reaction formula: Reactants are amine:COC1=NC(=NC=C1Br)N, amount is: 0.0009899999713525176 MOLE;aryl halide:C1=CC(=CC(=C1)I)C(F)(F)F, amount is: 0.0011899999808520079 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0011899999808520079 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 4.949999856762588e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 4.949999856762588e-05 MOLE.Products are 0:COC1=NC(=NC=C1Br)NC2=CC=CC(=C2)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: repeat of _EN06995-58\Reaction_ but using Xantphos **_Aim:-_ prepare target for further use.** 1-iodo-3-(trifluoromethyl)benzene (0.171 ml, 1.19 mmol), 5-bromo-4-methoxypyrimidin-2-amine (0.202 g, 0.99 mmol), PALLADIUM(II) ACETATE (0.011 g, 0.05 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) - Xantphos (0.029 g, 0.05 mmol) and cesium carbonate (0.387 g, 1.19 mmol) were mixed in toluene (5ml), purged with nitrogen and stirred in a sealed tube at 90 °C overnight. LCMS: pH = 3, 2 minute run time, shows sign of product at Rt = 1.41 min The reaction mixture was diluted with EtOAc (20 ml), filtered through a celite pad and concentrated to give 477 mg yellow solid. TLC (1:1 - EtOAc : n-heptane) see diagram UV only This was disolved in DCM, absorbed onto a samplet and purified on a 10 g Biotage SNAP column (approx column volume = 7 ml), eluting with a step-wise gradient from 0 : 10 to 4 : 6 EtOAc : n-heptane using a Thomson pump collecting 12 ml fractions. F1 - y = 149 mg - GCMS (Steep_10 min), Rt = 7.88 min (100%) m/z: 346/8. LCMS of F2 did not show anything of interest! **_Conclusion:_ \- ** Seems like xanphos works but could be better - used in EN06995-68 |
Here is a chemical reaction formula: Reactants are aryl halide:CC1=CN=C(N=C1C2=CN3C[C@H](N(C(=O)C3=N2)CC4=CC(=C(C=C4)F)F)COC)Cl, amount is: 0.0011899999808520079 MOLE;amine:CN1C(=CC=N1)N, amount is: 0.0009899999713525176 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.008999999612569809 MOLE,this reaction does not need solvents,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.0003000000142492354 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0003000000142492354 MOLE.Products are 0:CC(C)CN(C1=CC(=C(N=C1)C(=O)[C@H]2C[C@@H]2C(=O)O)OC)C3=C(C=CC(=C3)C(F)(F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 18-mar-2014 17:15:52 +0100, blandar allt, add toluen, N2 flushar - rör 110 gC/ön/N2. Nästa em kl 16, fått svalna - LCMS ser bra ut, 17:49:27 - nu hydrolys/rt, klart efter 90 min ca, slår på 600 uL HoAc, evap. Till SSL, 24-mar-2014 190 mg åter från SSL. ( 1 g CBA prekond MeOH, löser i några ml ACN, eluerar mha 2.5 överkolonn vol, späder med avjonat aq, lyoph ön) HNMR OK LCMS OK |
Here is a chemical reaction formula: Reactants are amine:CC(C)CNC1=C(C=CC(=C1)C(F)(F)F)F, amount is: 0.006000000052154064 MOLE;aryl halide:CCOC(=O)C1CC1C(=O)C2=C(C=C(C=N2)Br)OC, amount is: 0.006000000052154064 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0003000000142492354 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.0003000000142492354 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.0003000000142492354 MOLE.Products are 0:CC(C)CN(C1=CC(=C(N=C1)C(=O)[C@H]2C[C@@H]2C(=O)O)OC)C3=C(C=CC(=C3)C(F)(F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (allt satsas i Toluen, N2 bubblar) start 09-jun-2014 19:51:32 +0200. LCMS-1 1600 nästa em ser bra ut, hittar inga SM, får svalna - bryter. Späder med 30 ml etoac, filtrerar genom SiO plugg, evap. evap två gånger ur 30 ml THF, LCMS-2 visar P 10-jun-2014 19:15:25 +0200 löser i 20 ml THF, 10 ml MeOH, adderar LiOH(758 mg löst i 20 ml aq) - lösning, rör rt. Kl 1951 kör LCMS-3, ser riktigt bra ut, inga SM kvar ser det ut som. Ser ingen substitution F mot MeO. Kl 20.20 quench med 2 ml HOAc, evap hårt, m=5.0 g - till SSL. 16-jun-2014 11:32:38 +0200 nu fått åter 1.4 g dygt från SSL samt även dess enantiomer. Tar det via pulvret och kör HNMR (3.5 mg i DMSO). Visar rester från upprening, sätter kl 12.07 på indunstaren med fullt vakuum 60 grC badT samt kolsyreis/aceton kylning få förlaget. Går fram till 1335, sedan rt 10 min.Går över till PARD med hela batchen. kristallin, får tillbaks återstod m=793 mg till CM 17-jun-2014 19:13:19 +0200. även R.R isomeren i betydlig mängd från SSL, användes först för att träna krist med 90/10 aq/etoh enligt recept, ser ok ut men mycket skumning. Dag senare slår på några ml iPrOH ser svårlösligt ut, add aning aq uppskattningsvis 80 iPrOH 20 aq, ser lite dimmigt utvärmer 70 gRC olja under omrn 5 min, mindre dimma?, står något litet faller ut sanbbt men kommer ej längre evap, faller vit/s - kristallin? Värmer 60 grC med CO2 aceton förlag 1 h.Får ihop 128 mg ser bra ut (krist). För för märkning och kristallinitet, visar sig vara kristallin och bra. Ger allt till så länge. |
Here is a chemical reaction formula: Reactants are amine:CN1C(=CC=N1)N, amount is: 0.00761000020429492 MOLE;aryl halide:CC1=CN=C(N=C1C2=CN3C[C@H](N(C(=O)C3=N2)CC4=CC(=C(C=C4)F)F)COC)Cl, amount is: 0.00506999995559454 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.010099999606609344 MOLE,Solvents are Solvent:CC1CCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4, amount is: 0.00040600000647827983 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 0.00020300000323913991 MOLE.Products are 0:CC1=CN=C(N=C1C2=CN3C[C@H](N(C(=O)C3=N2)CC4=CC(=C(C=C4)F)F)COC)NC5=CC=NN5C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2016-05-18 **time temp comment** 1 14:20 21 (S)-2-(2-chloro-5-methylpyrimidin-4-yl)-7-(3,4-difluorobenzyl)-6-(methoxymethyl)-6,7-dihydroimidazo[1,2-a]pyrazin-8(5H)-one (2.2 g, 5.07 mmol), 1-methyl-1H-pyrazol-5-amine (0.754 g, 7.61 mmol) and cesium carbonate (3.30 g, 10.14 mmol) was charged to a 100mL reactor. 2-methyl tetrahydrofuran (1.2 L) and water (0.120 L) was charged. Degassed (6x vac/N2) 14:25 21 2'-(dicyclohexylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine (dave phos) (0.160 g, 0.41 mmol) and Pd2dba3 (0.186 g, 0.20 mmol) was added. degassed (6x vac/N2). 14:25 21 heated to 80 magnetic stirrer under nitrogen. IPC1 (1,5h) SFC-MS indicates 9.5% conversion. 2016-05-19 08:00 reflux IPC2 (18h) SFC-MS indicates 66% conversion. 14.00 reflux IPC3 (23h) SFC-MS indicates 72% conversion. The reaction mixture was cooled to 40°C and 1 eq. of catalyst and ligand was added, 0.17g Pd and 0.15g Davefos. degassed 6 times. Jacket to 80°C , stirred over night. 2016-05-20 07:45 reflux IPC4 42h complete conversion. 1.19 g of silicycle was added and the temperature was set to ambient. . 10:18:07 rt the mixture was filtered through a celite filter (25µ). the filter cake was washed with EtOAc (2x 10 ml). 10:30:44 rt the filtrate was transfered to a sep funnel and washed with aq citric acid (0,5M, 15 ml) and water (5 ml). Unfortunately when washing with water some diluted HCl was used, so the reaction mixture was basified with bicarbonate solution prior to the final water wash. The organic layer was evaporated to a solid, 2.7g Material sent to SSL for separation 2016-05-23. Yield after chromatography: 1.38g |
Here is a chemical reaction formula: Reactants are amine:C(CN)C(=O)N.Cl, amount is: 0.0006220000213943422 MOLE;aryl halide:C1=CC(=CC=C1C(=O)O)Br, amount is: 0.0004970000009052455 MOLE,Reagents are Base:[Li+].C[Si](C)(C)[N-][Si](C)(C)C, amount is: 0.0011899999808520079 MOLE,Solvents are Solvent:C1CCOC1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 4.999999873689376e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 4.999999873689376e-05 MOLE.Products are 0:C1=CC(=CC=C1C(=O)O)NCCC(=O)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Palladium (II) acetate (0.011 g, 0.05 mmol) was added to(R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine (0.027 g, 0.05 mmol) in THF (1 mL) in a reaction vessel evacuated and purged with nitrogen. The resulting catalyst mixture was stirred and under nitrogen at 50 °C for 30 minutes. 04-Dec-2013 10:52:28 AM -0500 LiHMDS (1.194 mL, 1.19 mmol), 3-aminopropanamide, HCl (0.077 g, 0.62 mmol) and 4-bromobenzoic acid (0.1 g, 0.50 mmol) was added to a second reaction vessel and purged with nitrogen. were added at 20 °C. The catalyst solution was added to the reaction mixture and the resulting mixture was stirred at 120 °C for 16 hours. LCMS showed starting material only. Desired product not isolated from this reaction. |
Here is a chemical reaction formula: Reactants are amine:C1COCCN1C2=CN=C(C=C2)N, amount is: 0.002689999993890524 MOLE;aryl halide:C1=CN2C=C(C=C(C2=N1)Br)Cl, amount is: 0.002240000059828162 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.00559999980032444 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 0.00044800000614486635 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 0.00033599999733269215 MOLE.Products are 0:C1COCCN1C2=CN=C(C=C2)NC3=CC(=CN4C3=NC=C4)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 8-bromo-6-chloroimidazo[1,2-a]pyridine, HCl (600mg, 2.24 mmol), 5-morpholinopyridin-2-amine (482 mg, 2.69 mmol), BINAP (279 mg, 0.45 mmol), cesium carbonate (1824 mg, 5.60 mmol) in Toluene (12 mL) was sparged with nitrogen while stirring for 10 minutes. palladium(II) acetate (87 mg, 0.39 mmol) was then added and the reaction stirred at 105 °C for overnight. At ths stage LC/MS indicated that formation of the product. After this time, the reaction was cooled to room temperature, diluted with mixture of 1:1 methanol/DCM ( 100 mL) and filtered through celite. The filtrated concentrated under reduced pressure and the resulting residue purified by flash chromatography (silicagel, 0-10% DCM/Methanol, 25 minutes) to afford 6-chloro-N-(5-morpholinopyridin-2-yl)imidazo[1,2-a]pyridin-8-amine (482 mg, 65.3 %) as a solid. LC/MS (2 minute, Acid _CV10.olp method 330 (M + 1), 0.66 minutes. 1H NMR (400 MHz, DMSO- _d_ 6) d ppm 9.16 (s, 1 H) 8.30 - 8.34 (m, 1 H) 8.25 - 8.29 (m, 1 H) 7.98 - 8.03 (m, 1 H) 7.88 - 7.92 (m, 1 H) 7.54 - 7.57(m, 1 H) 7.36 - 7.47 (m, 2 H) 3.72 - 3.79 (m, 4 H) 3.05 - 3.12 (m, 4 H) |
Here is a chemical reaction formula: Reactants are amine:C1C[C@H](C(=O)NC1)N, amount is: 0.0010400000028312206 MOLE;aryl halide:C1=CC(=C(N=C1)Br)Cl, amount is: 0.0010400000028312206 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0018100000452250242 MOLE,Solvents are Solvent:CC1=CC=CC=C1, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 1.5600000551785342e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 7.900000127847306e-06 MOLE.Products are 0:C1C[C@H](C(=O)NC1)NC2=C(C=CC=N2)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In a 5 ml MW vial, Pd2((dba)3 (7.23 mg, 7.90 µmol), 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (9.71 mg, 0.02 mmol), sodium 2-methylpropan-2-olate (174 mg, 1.81 mmol), (R)-3-aminopiperidin-2-one (119 mg, 1.04 mmol) and 2-bromo-3-chloropyridine (200 mg, 1.04 mmol) mixed in toluene (2 mL) to give a brown suspension. The mixture was degassed with N2 bubbling for 5 min, then the vial was capped and the reaction stirred at 115°C in an oil-bath over night. The reaction was cooled to rt, DCM and aq NaHCO3 were added, the mixture stirred, filtered through a phase separator and evaporated. LC-MS crude: Traces of product, mainly starting bromide left. Reaction discarded. |
Here is a chemical reaction formula: Reactants are amine:C1=CC(=C(C(=C1)F)CN)F, amount is: 0.0005370000144466758 MOLE;aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0009769999887794256 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 5.999999848427251e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.909999941242859e-05 MOLE.Products are 0:C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=C(C=CC=C3F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (2,6-difluorophenyl)methanamine (77 mg, 0.54 mmol), 4-chloro-N- phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was heated thermally to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Fractions containing product were evaporated to dryness to afford N4-(2,6-difluorobenzyl)-N2-phenylpyridine-2,4-diamine (93 mg, 61.1 %) as a purple gum. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE;amine:C1=CC(=C(C(=C1)F)CN)F, amount is: 0.0006350000039674342 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0009769999887794256 MOLE,Solvents are Solvent:COCCOC, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 5.999999848427251e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 3.909999941242859e-05 MOLE.Products are 0:C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=C(C=CC=C3F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-chloro-N-phenylpyridin-2-amine (100 mg, 0.49 mmol), (2,6-difluorophenyl)methanamine (91 mg, 0.64 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol),sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were suspended in DME (2.0 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 20 minutes in the microwave reactor and cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness to afford crude product. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5µ silica, 50 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford N4-(2,6-difluorobenzyl)-N2-phenylpyridine-2,4-diamine (32.0 mg, 21.04 %) as a yellow gum. |
Here is a chemical reaction formula: Reactants are aryl halide:CN1C[C@@H](OC2=C(C1)C=CC(=N2)Cl)C3=CC=CC=C3, amount is: 0.0007389999809674919 MOLE;amine:CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC, amount is: 0.0008870000019669533 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.002219999907538295 MOLE,Solvents are Solvent:COCCOC, amount is: 0.0 ,Catalysts are metal and ligand:C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4, amount is: 7.390000246232376e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 7.390000246232376e-05 MOLE.Products are 0:CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(CN(C[C@@H](O4)C5=CC=CC=C5)C)C=C3)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.213 g, 0.89 mmol), Palladium(II) acetate (0.017 g, 0.07 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.026 g, 0.07 mmol) and Cesium carbonate (0.722 g, 2.22 mmol) were put in a 20 mL microwave vial and sealed. The vial was flushed with argon. (S)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.203 g, 0.74 mmol) in DME (5 mL) was added and additional 5 mL was added to the vial. The reaction mixture was run in the microwave at 100°C for 80 minutes. Reaction still not complete. Additional palladium(II)acetate (0.1 eq) and 2-(dicyclohexylphosphino)biphenyl (0.1 eq) were added and the reaction was run again in the microwave for 60 minutes. Have about 14% oxazepine left. Heated for additional 45 minutes. 10% oxazepine left. Added 0.1 eq palladium(II)acetate, 0.1 eq 2-(dicyclohexylphosphino)biphenyl and 0.3 eq of 3-methoxy-4-(4-methyl-1Himidazol-1-yl)aniline and let the reaction run in the microwave for additional 60 minutes. The reaction mixture was filtrated through celite, concentrated and purified first by silica flash chromatography using methanol in dichlorometane (0 to 4%). The productcontaining fractions were pooled and purified further by preparative chromatography. The productcontaining fractions were pooled, concentrated and partitioned between sat. NaHCO3 (aq) and dichloromethane. The organic layer was washed with brine, dried (MgSO4) and concentrated giving 0.091 g of the product. |
Here is a chemical reaction formula: Reactants are aryl halide:C1=C(C=C(C=C1F)Br)F, amount is: 7.400000322377309e-05 MOLE;amine:CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3)OC(=CC2=O)N4CCOCC4, amount is: 6.730000313837081e-05 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.00010099999781232327 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 3.370000058566802e-06 MOLE;metal and ligand:CC1(C2=C(C(=CC=C2)[PH+](C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5[PH+](C6=CC=CC=C6)C7=CC=CC=C7)C.C1=[C-]C=C(C=C1F)F.Br[Pd+], amount is: 3.370000058566802e-06 MOLE.Products are 0:CN(C)C(=O)C1=CC2=C(C(=C1)C3CCCN3C4=CC(=CC(=C4)F)F)OC(=CC2=O)N5CCOCC5, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Pd complexe (2.96 mg, 3.37 µmol) was added to a stirred mixture of N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (25 mg, 0.07 mmol), 1-bromo-3,5-difluorobenzene (8.53 µl, 0.07 mmol) and cesium carbonate (32.9 mg, 0.10 mmol) dissolved in 1,4-dioxane (0.5 ml) under argon. The resulting suspension was degased with argon and then stirred at 80 °C for 3.5 hours. Lcms showed complete reaction. The reaction mixture was allowed to cool to room temperature, filtered and concentrated. The crude product was purified by preparative HPLC using a Waters X-Bridge reverse-phase column (5 microns silica, 30 mm diameter, 150 mm length) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The fractions were evaporated to dryness to afford 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (11.00 mg, 33.8 %) as a pale beige foam. LCMS and NMR are OK |
Here is a chemical reaction formula: Reactants are aryl halide:CC1=C(C=C(C=C1)C2=NC=CN2)NC(=O)C3=CC=C(C=C3)OCC4=C(C=CC=N4)Br, amount is: 0.00010800000018207356 MOLE;amine:CN1CCNCC1, amount is: 0.0003239999932702631 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.00021600000036414713 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8, amount is: 4.320000152802095e-05 MOLE;metal and ligand:C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd], amount is: 2.1600000764010474e-05 MOLE.Products are 0:CC1=C(C=C(C=C1)C2=NC=CN2)NC(=O)C3=CC=C(C=C3)OCC4=C(C=CC=N4)N5CCN(CC5)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N-(5-(1H-imidazol-2-yl)-2-methylphenyl)-4-((3-bromopyridin-2-yl)methoxy)benzamide (50 mg, 0.11 mmol), 1-methylpiperazine (32.4 mg, 0.32 mmol), Pd2(dba)3 (19.76 mg, 0.02 mmol) and BINAP (26.9 mg, 0.04 mmol), CS2CO3 (70.3 mg, 0.22 mmol) in DMA (5 mL) was stirred at 100 °C for overnight. LCMS didn't mornitor the desired product. |
Here is a chemical reaction formula: Reactants are amine:CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)N, amount is: 0.0009539999882690609 MOLE;aryl halide:C1CCN2C(=C(C=N2)C3=CC(=NC=C3F)Cl)C1, amount is: 0.0007949999999254942 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.0023799999617040157 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C, amount is: 0.00015900000289548188 MOLE;metal and ligand:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd], amount is: 7.950000144774094e-05 MOLE.Products are 0:CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H](C1)C(=O)NC2=NC=C(C(=C2)C3=C4CCCCN4N=C3)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Tetrakis(triphenylphosphine)palladium(0) (0.092 g, 0.08 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine (0.200 g, 0.79 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (0.231 g, 0.95 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.092 g, 0.16 mmol) and Cesium carbonate (0.777 g, 2.38 mmol) in 1,4-dioxane (5.98 ml). Degassed for 5 mins under nitrogen and the resulting suspension was stirred at 120 °C for 2 hours in the microwave reactor. The reaction mixture was partitioned between water (20ml) and DCM (40ml) and separated using a phase separation cartridge. The organics were absorbed onto silica and purified by flash silica chromatography, elution gradient 0 to 60% EtOAc in heptane. Still impure but telescoped through to next stage without further purification. (136mg). |
Here is a chemical reaction formula: Reactants are amine:CC(C1=NC=C(C=N1)F)N.Cl, amount is: 0.0014199999859556556 MOLE;aryl halide:CN1C=C(N=C1)NC2=C3C=CN(C3=NC(=N2)Cl)C4CC4, amount is: 0.0007099999929778278 MOLE,Reagents are Base:C(=O)([O-])[O-].[Cs+].[Cs+], amount is: 0.004970000125467777 MOLE,Solvents are Solvent:C1COCCO1, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 0.00011000000085914508 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 7.000000186963007e-05 MOLE.Products are 0:CC(C1=NC=C(C=N1)F)NC2=NC(=C3C=CN(C3=N2)C4CC4)NC5=CN(C=N5)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 1-(5-fluoropyrimidin-2-yl)ethanamine hydrochloride (252 mg, 1.42 mmol), 2-chloro-7-cyclopropyl-N-(1-methyl-1H-imidazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (205 mg, 0.71 mmol), palladium(II) acetate (15.94 mg, 0.07 mmol) and palladium(II) acetate (15.94 mg, 0.07 mmol) (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (62.1 mg, 0.11 mmol) and CS2CO3 (1619 mg, 4.97 mmol) in 1,4-dioxane (4733 µl) was heatd to 150 oC for 20 min with well-stirring. Reaction was diluted with DCM/MeOh (10%) the organic layer was washed with water. And concntraction provided product. Reaction is clean and 70% contaminated with hydroxy product (P3). Reaction was purified on gilsen (5 to 45%) provide product 40 mg. Compound was submitted to chiral purification. Chiral sepreation: En02021-65-2 (P2, E1) : EN02021-65-3 (P3, E2) = 4:96 There is no racemization observed in reaction. |
Here is a chemical reaction formula: Reactants are amine:COC1=CC=CC(=C1)CN, amount is: 0.0005370000144466758 MOLE;aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, amount is: 0.0004889999981969595 MOLE,Reagents are Base:CC(C)(C)[O-].[Na+], amount is: 0.0009769999887794256 MOLE,Solvents are Solvent:CC(=O)N(C)C, amount is: 0.0 ,Catalysts are metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe], amount is: 5.999999848427251e-05 MOLE;metal and ligand:CC(=O)O.CC(=O)O.[Pd], amount is: 5.999999848427251e-05 MOLE.Products are 0:COC1=CC=CC(=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (3-methoxyphenyl)methanamine (73.7 mg, 0.54 mmol), 4-chloro-N- phenylpyridin-2-amine (100 mg, 0.49 mmol) and sodium 2-methylpropan-2-olate (94 mg, 0.98 mmol) were suspended in DMA (2 mL) and sealed into a microwave tube. Nitrogen was bubbled through the reaction mixture for 5 minutes. (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (32.5 mg, 0.06 mmol) and diacetoxypalladium (8.78 mg, 0.04 mmol) were added to the reaction mixture and nitrogen was bubbled through the reaction mixture for a further 5 minutes. The reaction was heated thermally to 100 °C for 30 mins under nitrogen and cooled to RT. The reaction mixture was neutralised with HCl and purified by ion exchange chromatography, using a 20 g SCX column. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Fractions containing product were evaporated to dryness to afford N4-(3-methoxybenzyl)-N2-phenylpyridine-2,4-diamine (80 mg, 53.6 %) as an off-white gum. |