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Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC=NC(=C1)Cl;amine:CC(C)(C)OC(=O)N1CCC[C@H](C1)N, Reagents are:Solvent:CC1=CC=CC=C1;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;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];Base:CC(C)(C)[O-].[Na+], and Products are 0:CC(C)(C)OC(=O)N1CCC[C@H](C1)NC2=CC=CC=N2, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Vial 1) Pd2(dba)3 (0.018 g, 0.02 mmol) and BINAP (0.024 g, 0.04 mmol) were mixed in toluene (1mL) under N2 and stirred at rt for 5min. Vial 2) sodium tert-butoxide (0.999 g, 10.08 mmol), tert-butyl (R)-3-aminopiperidine-1-carboxylate (1.249 g, 6.05 mmol) and 2-chloropyridine (0.477 mL, 5.04 mmol) were mixed in toluene (6mL) under N2. Added the catalyst solution from vial 1. The mixture was heated at 110°C in an oil-bath. LCMS (3h): product, no SM left. The reaction was cooled to rt and the solvent was evaporated. Added EtOAc, washed with water. Purified by column chromatography (using SP4 TM HPFC system, KP-Sil (50g) column, A=heptane, B=EtOAc/2M NH3 in MeOH (9/1), 27mL/fr, (0% B 2CV, 0-30% B 10CV, 30% B 2CV)) to yield tert-butyl (R)-3-(pyridin-2-ylamino)piperidine-1-carboxylate (1.306 g, 93 %) as yellow solid. [M+H]+ 278. 1H NMR (400 MHz, CDCl3) d 1.42 (s, 9H), 1.51 - 1.64 (m, 2H), 1.68 - 1.8 (m, 1H), 1.93 - 2.05 (m, 1H), 2.81 - 3.36 (m, 2H), 3.45 - 4.16 (m, 3H), 4.50 (d, 1H), 6.42 (d, 1H), 6.5 - 6.62 (m, 1H), 7.36 - 7.45 (m, 1H), 8.02 - 8.13 (m, 1H). Expected Number of Hs: 23 Assigned Hs: 23.

Here is a chemical reaction formula: Reactants are:amine:C1=CN=CC=C1CN;aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, Reagents are:Solvent:CC(=O)N(C)C;Base:CC(C)(C)[O-].[Na+];metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe];metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC=NC=C3, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Pyridin-4-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 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 N2-phenyl-N4-(pyridin-4-ylmethyl)pyridine-2,4-diamine (39.8 mg, 29.5 %) as an off white gum.

Here is a chemical reaction formula: Reactants are:amine:C1=CN=CC=C1CN;aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, Reagents are:metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe];metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:CC(C)(C)[O-].[Na+];Solvent:CC(=O)N(C)C, and Products are 0:C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC=NC=C3, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Pyridin-4-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 impure product. Impure product was purified by flash silica chromatography, elution gradient 3 to 8% MeOH in DCM. Fractions containing product were evaporated to dryness to afford impure product. Impure 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 N2-phenyl-N4-(pyridin-4-ylmethyl)pyridine-2,4-diamine (31.2 mg, 23.11 %) as an off white solid.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC(=CC(=C1)Br)[N+](=O)[O-];amine:CC(C)(C)OC(=O)NC1CCNCC1, Reagents 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;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];Base:C(=O)([O-])[O-].[Cs+].[Cs+];Solvent:CC1=CC=CC=C1, and Products are 0:CC(C)(C)OC(=O)NC1CCN(CC1)C2=CC(=CC=C2)[N+](=O)[O-], please give me the reaction condition of this formula.

The condition of this chemical reaction is: A 100 mL round bottom flask was charged with a magnetic stir bar, 1-bromo-3-nitrobenzene (1.000 g, 4.95 mmol), [Reactants], Pd2dba3 (0.227 g, 0.25 mmol), BINAP (0.308 g, 0.50 mmol), Cs2CO3 (4.03 g, 12.38 mmol), and toluene (19.80 ml). The vessel was capped with a septum, placed under an atmosphere of argon, and placed in an oil bath heated to 95 °C. The reaction was allowed to stir at this temperature for 16 h before being allowed to cool to rt. The reaction mixture was poured into a separatory funnel containing water (~100 mL) and extracted with ethyl acetate ( 2 x 100 mL). The combined organic extract was dried with MgSO4, filtered, and conc. _in vacuo_ to yield the crude product which was purified via silica gel chromatography (80 g) using ethyl acetate/hexanes (1:5) as eluent to provide pure tert-butyl 1-(3-nitrophenyl)piperidin-4-ylcarbamate (0.901 g, 56.6 %) as a light yellow solid.

Here is a chemical reaction formula: Reactants are:amine:C[C@@H]1CNCCN1;aryl halide:CC(=O)OCC1=C2C(=CC=C1)C(=O)C=C(O2)C3=CC=C(C=C3)Br, Reagents are:Solvent:CC1=CC=CC=C1;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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:C[C@@H]1CN(CCN1)C2=CC=C(C=C2)C3=CC(=O)C4=CC=CC(=C4O3)CO, please give me the reaction condition of this formula.

The condition of this chemical reaction is: diacetoxypalladium (6.02 mg, 0.03 mmol) was added to a degassed mixture of (2-(4-bromophenyl)-4-oxo-4H-chromen-8-yl)methyl acetate (200 mg, 0.54 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (25.03 mg, 0.04 mmol) and cesium carbonate (244 mg, 0.75 mmol) in toluene (5 mL). The resulting suspension was stirred at 110 °C for 3 hours under nitrogen (see note 1). More diacetoxypalladium (6.02 mg, 0.03 mmol) was added and the reaction mixture was heated to 110°C for 1 hour and again could see no product. TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (4.91 mg, 5.36 µmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (25.03 mg, 0.04 mmol) were added and the reaction mixture was heated to 110°C for 1 hour and again could see no product. sodium 2-methylpropan-2-olate (61.8 mg, 0.64 mmol) was added and the reaction mixture was heated to 110°C for 1 hour where a small amount of product could be detected by LCMS and significant dehalogenation. The reaction mixture was allowed to cool to room temperature 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 flash silica chromatography, elution gradient 0 to 5% 7N NH3/MeOH in DCM. Fractions were evaporated to dryness to afford product that was not pure. The sample was dissolved in DMF (4ml) and the crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5µ silica, 30 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 (R)-8-(hydroxymethyl)-2-(4-(3-methylpiperazin-1-yl)phenyl)-4H-chromen-4-one (25.00 mg, 13.31 %) as a yellow solid.

Here is a chemical reaction formula: Reactants are:aryl halide:C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl;amine:CC1=CC(=C(C=C1NC(=O)C)N)F, Reagents are:Solvent:C1COCCO1;metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C;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];Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:CC1=CC(=C(C=C1NC(=O)C)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: In 20 ml microwave vial were added 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (200 mg, 0.86 mmol), N-(5-amino-4-fluoro-2-methylphenyl)acetamide (164 mg, 0.90 mmol), Pd2dba3 (39.2 mg, 0.04 mmol), di-tert- butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (37.5 mg, 0.09 mmol) and Cs2CO3 (837 mg, 2.57 mmol). The vessel was fitted with septum, gas inlet and dioxane (8 mL) was added via syringe. The resulting suspension was stirred for 5 min. under N2. The septum and gas inlet quickly replaced with microwave vial cap and the mixture was heated to 150oC under microwave irradiation for 30 min. The reaction mixture filtered through celite, filtrate concentrated, combined with EN02368-53 experiment and purified by ISCO column (0-5% MeOH-CH2Cl2). The obtained compound triturated with CH3CN, filtered and dried to give light brown color solid. Conclusion: product isolated

Here is a chemical reaction formula: Reactants are:amine:C1COCCN1;aryl halide:CCOC(=O)C1=CC(=CC=C1)Br, Reagents are:Base:C(=O)([O-])[O-].[Cs+].[Cs+];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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Solvent:CC1=CC=CC=C1, and Products are 0:CCOC(=O)C1=CC(=CC=C1)N2CCOCC2, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A mixture of ethyl 3-bromobenzoate (0.070 mL, 0.44 mmol), cesium carbonate (427 mg, 1.31 mmol), diacetoxypalladium (4.90 mg, 0.02 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (5.44 mg, 8.73 µmol) and morpholine (0.042 mL, 0.48 mmol) in toluene (2 mL) was refluxed for 1h. The reaction mixture was cooled and filtered through celite. The celite was washed with EtOAc. The solvent was removed under reduced pressure. The residue was purified by automated flash chromatography on a SNAP 25 g column. A gradient from 0% to 50% of EtOAc in Heptane over 10CV was used as mobile phase. The product was collected using the wavelength 254 nm.

Here is a chemical reaction formula: Reactants are:amine:CC(C)(C)OC(=O)N1CCNCC1;aryl halide:C1=CC(=CN=C1)Br, Reagents are:Solvent:C1COCCO1;metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:CC(C)(C)[O-].[Na+], and Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=CN=CC=C2, please give me the reaction condition of this formula.

The condition of this chemical reaction is: diacetoxypalladium (0.072 g, 0.32 mmol) and RuPhos (0.301 g, 0.64 mmol) were stirred in 1,4-dioxane (11.36 ml) for 10 mins at 50 °C.tert-butyl piperazine-1-carboxylate (0.6 g, 3.22 mmol), 3-bromopyridine (0.310 ml, 3.22 mmol) and sodium tert-butoxide (0.464 g, 4.83 mmol) were added and the reaction mixture was stirred at 100 °C for 64 h. The reaction mixture was filtered through celite. 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-(pyridin-3-yl)piperazine-1-carboxylate (0.322 g, 38.0 %) as a yellow oil which crystallised on standing. This was then combined with EN06111-39-01.

Here is a chemical reaction formula: Reactants are:amine:CC(C)(C)OC(=O)N1CCNCC1;aryl halide:C1=CC(=CN=C1)Br, Reagents are:Base:CC(C)(C)[O-].[Na+];Solvent:CC1=CC=CC=C1;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;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], and Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=CN=CC=C2, please give me the reaction condition of this formula.

The condition of this chemical reaction is: TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.059 g, 0.06 mmol) and rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.080 g, 0.13 mmol) were mixed together and evacuated and purged with nitrogen 3 times. toluene (31.6 ml) was added and the resulting mixture heated to 90°C for 10 minutes then cooled to room temperature. sodium tert-butoxide (0.465 g, 4.84 mmol), 3-bromopyridine (0.310 ml, 3.22 mmol) and tert-butyl piperazine-1-carboxylate (0.6 g, 3.22 mmol) were added and the resulting mixture was heated at 85 °C for 64 hours. The reaction mixture was cooled to RT and filtered through celite and concentrated to give an orange solid. The crude product was purified by flash silica chromatography, elution gradient 30 to 50% EtOAc in heptane. Pure fractions were evaporated to dryness to afford tert-butyl 4-(pyridin-3-yl)piperazine-1-carboxylate (0.248 g, 29.2 %) as a yellow oil which crystallised on standing.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC=C(C=C1)Br;amine:C1=CC(=CC(=C1)N)CO, Reagents are:Base:C(=O)([O-])[O-].[Cs+].[Cs+];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;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];Solvent:C1CCOC1, and Products are 0:C1=CC=C(C=C1)NC2=CC=CC(=C2)CO, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A solution of Tris(dibenzylideneacetone)dipalladium(0) (0.178 g, 0.19 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.282 g, 0.49 mmol) in THF (20 mL) (degassed) was heated to 50 ºC under a nitrogen atmosphere for 30 min. (3-(phenylamino)phenyl)methanol (0.072 g, 11.13 %) (0.4 g, 3.25 mmol) and cesium carbonate (2.117 g, 6.50 mmol) were added followed by bromobenzene (0.409 mL, 3.90 mmol) and the mixture stirred at 65 °C over two days. The reaction mixture was cooled to room temperature then diluted with DCM and filtered. stirred with SiliCycle SiliMet-SH (1 g) for 3 h at 60 °C. The mixture was filtered through an acrodisc glassfiber filter, 25 mm, 1.0 µm. The filtrate (clear) was concentrated to give crude product (1,00 g). The crude was dissolved in DMSO and the product was purified by prep-HPLC on a Kromasil C8 column (10 µm 250x50 ID mm) using a gradient of 5-65% acetonitrile in H2O/ACN/HOAc 95/5/0.2 buffer over 30 minutes with a flow of 100 mL/min. The compounds were collected on UV at 303 nm, threshold 1000. The product containing fractions were pooled and concentrated on the rotavapor. Toluene was added and evaporated to get rid of residue of water to give the product (3-(phenylamino)phenyl)methanol (0.072 g, 11.13 %) as a transparent oil.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC(=CC(=C1)I)C(F)(F)F;amine:COC1=NC(=NC=C1Br)N, Reagents are:Solvent:CC1=CC=CC=C1;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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:COC1=NC(=NC=C1Br)NC2=CC=CC(=C2)C(F)(F)F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: _EN06995-11\Reaction_ and many others **_Aim:-_ prepare target for further use.** 1-iodo-3-(trifluoromethyl)benzene (0.215 ml, 1.49 mmol), 5-bromo-4-methoxypyrimidin-2-amine (0.254 g, 1.24 mmol), PALLADIUM(II) ACETATE (0.014 g, 0.06 mmol), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (0.054 g, 0.09 mmol) and cesium carbonate (0.487 g, 1.49 mmol) were mixed in toluene (5ml), purged with nitrogen and stirred in a sealed tube at 80 °C overnight. LCMS: pH = 3, 2 minute run time, Rt = 0.66 min (32% by UV), m/z: 204 (MH+) \- 316 (M-H-) - ?; Rt = 1.10 min (15% by UV), m/z: 257, 306 (MH+) - 316 (M-H-) - ?; Rt = 1.28 min (25% by UV), m/z: 350, (MH+) product ?. The reaction mixture was diluted with EtOAc (20 ml), filtered through a celite pad and concentrated to give 902 mg yellow oil. 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 = 38 mg - GCMS and NMR - show it to be product F2 - y = 229 mg \- GCMS and NMR - show it to be bromo SM **_Conclusion:_ \- ** Abandoned - to be repeated with xanphos

Here is a chemical reaction formula: Reactants are:aryl halide:CN1CCN(CC1)C2=C3CN(CCC3=C(C=C2)OC)C(=O)CC4=CC=C(C=C4)Br;amine:C1CCNCC1, Reagents are:Solvent:COCCOC;Base:CC(C)(C)[O-].[Na+];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;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], and Products are 0:CN1CCN(CC1)C2=C3CN(CCC3=C(C=C2)OC)C(=O)CC4=CC=C(C=C4)N5CCCCC5, please give me the reaction condition of this formula.

The condition of this chemical reaction is: 2-(4-bromophenyl)-1-(5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (125 mg, 0.27 mmol),[Reactants],piperidine (23.22 mg, 0.27 mmol) was taken in a mixture of DME (5 mL):water (1.250 mL) under N2.The reaction mixture was purged under N2 for 10 min.Tris(dibenzylideneacetone)dipalladium (0) (14.98 mg, 0.02 mmol) was added to the above reaction.The resulting reaction was stirred for 3 hrs at reflux tempt.LCMS profile showed formation of required product.Reaction was cooled to rt,solvents was evapourated to dryness.Crude was diluted with DCM and water (min) and organic layer separated and concentrated .Purification was done on RP systme to get product 1-(5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydroisoquinolin-2(1H)-yl)-2-(4-(piperidin-1-yl)phenyl)ethanone as a solid.but the product was not submitted due to very less ammount.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC=C2C(=C1)C(=CN=N2)Cl;amine:CN1C(=C(C=N1)C(=O)N2CCC(CC2)N)Cl, Reagents are:Base:C(=O)([O-])[O-].[Cs+].[Cs+];Solvent:CC1=CC=CC=C1;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;metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:CN1C(=C(C=N1)C(=O)N2CCC(CC2)NC3=CN=NC4=CC=CC=C43)Cl, please give me the reaction condition of this formula.

The condition of this chemical reaction is: (4-aminopiperidin-1-yl)(5-chloro-1-methyl-1H-pyrazol-4-yl)methanone (442 mg, 1.82 mmol) was taken in a microwave tube. Added racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (113 mg, 0.18 mmol) followed by the addition of Palladium (II) acetate (40.9 mg, 0.18 mmol), racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (113 mg, 0.18 mmol), Cesium carbonate (1782 mg, 5.47 mmol) and diisopropylethyl amine(1ml). toluene (10 mL) was added and stirred at 140 °C for 8h. After the completon of the reaction adsorbed the reaction mass on silica gel and purified by silica gel column.

Here is a chemical reaction formula: Reactants are:aryl halide:CN1CC(OC2=C(C1=O)C=CC(=N2)Cl)C3=CC=CC=C3;amine:CC1=CN(C=N1)C2=C(C=C(C=C2)N)OC.Cl, Reagents are:Solvent:COCCOC;metal and ligand:C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:CC1=CN(C=N1)C2=C(C=C(C=C2)NC3=NC4=C(C=C3)C(=O)N(CC(O4)C5=CC=CC=C5)C)OC, please give me the reaction condition of this formula.

The condition of this chemical reaction is: were placed in a microwave vial equipped with a stirring bar. The vial was capped and flushed with argon. DME (2 mL) and Et3N (0.028 mL, 0.20 mmol) were added via a syringe and the mixture was stirred at room temperature for 30 min and then heated to 100°C in a microwave apparatus for 1h. The reaction mixture was diluted with dichloromethane and ethyl acetate, fitered and concentrated. The residue was purified by reversed phase HPLC to give 37 mg of the product as a solid.

Here is a chemical reaction formula: Reactants are:aryl halide:C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl;amine:CC(=O)NC1=C(C=CC(=C1)N)N(C)CCN(C)C, Reagents are:Solvent:C1COCCO1;Base:C(=O)([O-])[O-].[Cs+].[Cs+];metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C;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], and Products are 0:CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N(C)CCN(C)C, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Two reactions setup, each 600 mg scale. A 20 mL microwave reactor vial was charged with 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (1.2 g, 5.14 mmol), N-(5-amino-2-((2-(dimethylamino)ethyl)(methyl)amino)phenyl)acetamide (1.414 g, 5.65 mmol), 2-Di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl (0.218 g, 0.51 mmol), Pd2dba3 (0.235 g, 0.26 mmol) and CS2CO3 (5.02 g, 15.41 mmol). The vessel was fitted with a septum and gas inlet and dioxane (20 mL) was added via syringe. The resulting suspension was stirred for 5 min under nitrogen. The septum and gas inlet was quickly replaced with a microwave vial cap and the mixture was heated at 150 degrees under microwave irradiation for 1h. Two reactions combined and filtered through celite. The filtrate concentrated and submitted for purification (report attached). **Received a 3 different set up fractions:** First set up fractions (EN02868-04-1), LC-MS looks clean but 1H NMR shows acetate peak, couldn't getrid of it even longer time on lyohillizer. Second setup fractions combined, lyophllized, purified by ISCO column (0 - 20% MeOH-CH2Cl2 \+ 0.05% TEA). The obtained compound is a gum. It was triturated with 2 ml of EtOAc, formed a nice solid, it was filtered, washed with Et2O and dried to give 230 mg of white solid. 1H NMR showed slight shift of couple of peaks, it may be due to the protonation. 63 mg of this compound registered and submitted (EN02868-04-2). Third setup fractions showed no required product peaks, was discarded. EN02868-04-1, the remaining material after submission (EN02868-04-2), the filtrate of EN02868-04-2 combined, concentrated, treated with 3 g of MP- carbonate in THF (30 ml). After 1 h stirring, it was filtered washed with THF, concentrated, triturated with CH3CN, filtered and dried to give white color solid (EN02868-04-3). Conclusion: Product isolated

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC2=NC=CN2C=C1Br;amine:C1COCCN1, Reagents are:Base:C(=O)([O-])[O-].[Cs+].[Cs+];Solvent:C1COCCO1;metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4;metal and ligand:Cl[Pd+].C1=CC=C(C=C1)C2=CC=CC=C2N, and Products are 0:C1COCCN1C2=CN3C=CN=C3C=C2, please give me the reaction condition of this formula.

The condition of this chemical reaction is: 6-bromoimidazo[1,2-a]pyridine (299 mg, 1.52 mmol), dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (35.4 mg, 0.08 mmol), RuPhos 2nd generation (58.9 mg, 0.08 mmol), morpholine (0.159 ml, 1.82 mmol) and cesium carbonate (1483 mg, 4.55 mmol) were dissolved in degassed 1,4-dioxane (15.100 ml). Reaction mixture was purged with nitrogen for 2-3 minutes before heating to 90 °C and stirred under nitrogen overnight. The reaction was incomplete, therefore additional morpholine (0.159 ml, 1.82 mmol), RuPhos 2nd generation (58.9 mg, 0.08 mmol) and dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (35.4 mg, 0.08 mmol) were added and the reaction mixture washeated for a further 6.5 hours at 105°C. The reaction was still only ~20% complete therefore additional morpholine (0.318 ml), RuPhos 2nd generation (117.8 mg) and dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (70.8 mg) were added and the reaction heated for a further 24 hours at 105°C and then allowed to cool to RT. The residue partitioned between EtOAc and water, the organic phase was separated and the aq. rextracted with more EtOAc. The combined organic extracts were washed with brine, dried over magnesium sulfate filtered and evaporated. The crude material was purified by flash silica (12g, grace) chromatography, elution gradient 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford 4-(imidazo[1,2-a]pyridin-6-yl)morpholine (98 mg, 31.8 %) as a white solid.

Here is a chemical reaction formula: Reactants are:amine:C1CCC(CC1)N;aryl halide:CC1=C(N=CC=C1)Br, Reagents 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;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];Solvent:CC1=CC=CC=C1;Base:CC(C)(C)[O-].[Na+], and Products are 0:CC1=C(N=CC=C1)NC2CCCCC2, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Ref: EN07957-77 BIS(DIBENZYLIDENEACETONE)PALLADIUM(Pd2((dba)3) (0.101 g, 0.11 mmol) and 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (0.136 g, 0.22 mmol) was was stirred in toluene (16.5 mL) under N2. Then 2-bromo-3-methylpyridine (1.619 mL, 14.53 mmol), cyclohexanamine (1.662 mL, 14.53 mmol) and sodium 2-methylpropan-2-olate (2.430 g, 25.29 mmol) was added to the above reaction mixture under N2.The reaction mixture was degasssed by reapeated 3 times with N2 and vaccum before the reaction mixture was heated at 115 °C for 1.5h LCMS indicated no SM left. The reaction mixture was cooled to rt, and then diluted with EtOAc and H2O. and neutralized by citric acid to PH ca 5. The aqoeus phase was extracted with EtOAc (4 x). The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified automated flash chromatography on 100 g column. A gradient from 0 % to 30 % of EtOAc in heptane over 1800 mL was used as mobile phase. The product was collected using the wavelength 249 nm. Collect: F10, 0.231 g, light yellowish solid. LCMS ok, NMR ok F11-13: 1.398 g, light yellowish solid, LCMS ok, NMR ok F14-16, 79 mg, light yellowish solid, LCMS ok, NMR ok NMR of F11-13 1H NMR (500 MHz, DMSO) d 1.09 - 1.2 (m, 1H), 1.2 - 1.37 (m, 4H), 1.61 (d, 1H), 1.71 (d, 2H), 1.90 (d, 2H), 2.01 (s, 3H), 3.86 (ddd, 1H), 5.28 (d, 1H), 6.39 (dd, 1H), 7.09 - 7.22 (m, 1H), 7.83 (dd, 1H). Expected Number of Hs: 18 Assigned Hs: 18. [M + H]\+ 191.2

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC=C(C=C1)Br;amine:C1CC(NC1)C2=CC=CC=C2, Reagents are:Solvent:C1COCCO1;Base:C(=O)([O-])[O-].[Cs+].[Cs+];metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4;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], and Products are 0:C1CC(N(C1)C2=CC=CC=C2)C3=CC=CC=C3, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Caesium carbonate (553 mg, 1.70 mmol) was added to bromobenzene (0.059 mL, 0.57 mmol) and 2-phenylpyrrolidine (100 mg, 0.68 mmol) in 1,4-dioxane (2 mL). The reaction was degassed and Tris(dibenzylideneacetone)?dipalladium(0) (12.96 mg, 0.01 mmol) and dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (RuPhos) (13.21 mg, 0.03 mmol) were added. The resulting solution was stirred at 100 °C for 16 hours. LCMS showed the formation of the product. 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. NMR confirmed the presence of the product. The crude product was purified by flash silica chromatography, elution gradient 0 to 15% DCM in MeOH. Pure fractions were evaporated to dryness to afford 1,2-diphenylpyrrolidine (114 mg, 90 %) as a brown oil.

Here is a chemical reaction formula: Reactants are:aryl halide:CC1=CSC(=N1)Cl;amine:C1=CC=C(C=C1)CN, Reagents are:Base:CC(C)(C)[O-].[Na+];Solvent:CC(=O)N(C)C;metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe];metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:CC1=CSC(=N1)NCC2=CC=CC=C2, please give me the reaction condition of this formula.

The condition of this chemical reaction is: phenylmethanamine (100 mg, 0.93 mmol), 2-chloro-4-methylthiazole (125 mg, 0.93 mmol) and sodium 2-methylpropan-2-olate (179 mg, 1.87 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 (62.1 mg, 0.11 mmol) and diacetoxypalladium (16.76 mg, 0.07 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. No reaction. abandoned.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC(=NC=C1C(F)(F)F)Cl;amine:CCOC(=O)C1=CN=C(O1)N, Reagents are:Solvent:C1COCCO1;Base:C(=O)([O-])[O-].[Cs+].[Cs+];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;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], and Products are 0:CCOC(=O)C1=CN=C(O1)NC2=NC=C(C=C2)C(F)(F)F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Objective: Test of scope in the coupling of ester substituted aminooxazole To an oven-dried microwave vial was added ethyl 2-aminooxazole-5-carboxylate (156 mg, 1.00 mmol), 2-chloro-5-(trifluoromethyl)pyridine (181 mg, 1.00 mmol), cesium carbonate (651 mg, 2.00 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.87 mg, 0.02 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (43.4 mg, 0.075 mmol) and the vial was capped and purged with nitrogen. dioxane (4 mL) (degassed) was added and the reaction mixture was heated to 160 °C for 1 h under microwave irradiation. LCMS of the crude reaction mixture indicated that the desired product had been formed with very small amounts of side products apparent. DCM (20 mL) was added to the crude reaction mixture together with silica (2 g) and the solvent was removed from the reaction mixture under reduced pressure. The resulting residue was then placed in a dry-load tube prior to chromatography. The crude product was purified by flash silica chromatography, elution gradient 0 to 5% methanolic ammonia in DCM. Pure fractions were evaporated to dryness to afford the desired product in 74% yield and 92% purity by LCMS. The product was triturated with MeCN to give a solid which was collected by filtration and dried under vacuum to give ethyl 2-(5-(trifluoromethyl)pyridin-2-ylamino)oxazole-5-carboxylate (185 mg, 61.5 %) as a cream solid. This material was shown to be > 95% pure based on proton NMR strength. Conclusion: The desired product was formed in moderate yield and high purity.

Here is a chemical reaction formula: Reactants are:amine:C1=CC=C(C(=C1)CN)F;aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, Reagents are:metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe];metal and ligand:CC(=O)O.CC(=O)O.[Pd];Solvent:CC(=O)N(C)C;Base:CC(C)(C)[O-].[Na+], and Products are 0:C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC=CC=C3F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: (2-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-(2-fluorobenzyl)-N2-phenylpyridine-2,4-diamine (89 mg, 62.1 %) as a white solid.

Here is a chemical reaction formula: Reactants are:amine:CC1=CN(C=N1)C2=C(N=C(C=C2)N)OC;aryl halide:CC1=CN=C(S1)C2CN(CC3=C(O2)N=C(C=C3)Cl)C, Reagents are:Base:C(=O)([O-])[O-].[Cs+].[Cs+];Solvent:COCCOC;metal and ligand:C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4;metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:CC1=CN=C(S1)C2CN(CC3=C(O2)N=C(C=C3)NC4=NC(=C(C=C4)N5C=C(N=C5)C)OC)C, please give me the reaction condition of this formula.

The condition of this chemical reaction is: 8-chloro-4-methyl-2-(5-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (140 mg, 0.47 mmol), 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-amine (106 mg, 0.52 mmol), 2-(DICYCLOHEXYLPHOSPHINO)BIPHENYL (16.59 mg, 0.05 mmol), PALLADIUM(II) ACETATE (10.63 mg, 0.05 mmol) and Cs2CO3 (308 mg, 0.95 mmol) were weighed into a microwave vial, the vial was capped and DME (4 mL) was added. The vial was flushed with argon and heated to 100°C in a microwave reactor for 1 h. The reaction mixture was diluted with dichloromethane and filtered and the solvents were evaporated. The residue was purified by column chromatography on Silica using gradient elution with methanol in dichloromethane (0-6 %) to give N-(6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-4-methyl-2-(5-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine (162 mg, 73.8 %).

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC(=C(N=C1)Cl)Cl;amine:C1=CC=C(C=C1)C(=O)N, Reagents are:Base:C(=O)([O-])[O-].[Cs+].[Cs+];Solvent:C1COCCO1;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;metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:C1=CC=C(C=C1)C(=O)NC2=C(C=CC=N2)Cl, please give me the reaction condition of this formula.

The condition of this chemical reaction is: In a 5 mL vial were added Pd(OAc)2 (6.85 mg, 0.03 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (35.3 mg, 0.06 mmol), N-(3-chloropyridin-2-yl)benzamide (15.30 mg, 10.78 %) and cesium carbonate (477 mg, 1.46 mmol) in dioxane (2 mL) to give a yellow solution. The flask was evacuated and filled with Nitrogen three times. Then, 2,3-dichloropyridine (99 mg, 0.67 mmol) was added. The reaction mixture was stirred overnight at 80°C. The reaction mixture was diluted with EtOAc (3 mL) and filtered. The solid was washed with EtOAc and the collected organic layers were evaporated to dryness, to give the crude product. The compound was purified by preparative HPLC on a Kromasil C8 column (10 µm 250x20 ID mm) using a gradient of 10-50% acetonitrile in H2O/ACN/FA 95/5/0.2 buffer, over 20 minutes with a flow of 19 mL/min. The compounds were detected by UV at 230nm. (15,3 mg pure product). The reaction was repeated at 80C, RT and 110C on microwave, overnight and a weekend: the yield remains very low for all conditions except for the reaction at RT (no product at all).

Here is a chemical reaction formula: Reactants are:amine:CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2;aryl halide:C1=CN=C(C=C1C(F)(F)F)Cl, Reagents are:Solvent:CC1=CC=CC=C1;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;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];Base:CC(C)(C)[O-].[Na+], and Products are 0:CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2C3=NC=CC(=C3)C(F)(F)F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A 2.0-5.0 mL microwave vial was charged with (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (200 mg, 1.01 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (62.8 mg, 0.10 mmol), Sodium tert-butoxide (116 mg, 1.21 mmol), 2-Chloro-4-(trifluoromethyl)pyridine (0.156 mL, 1.21 mmol) and a mixture of toluene (2.5 mL) and DMF (.5 mL). The reaction mixture was degassed for 10 minutes with nitrogen, and then Tris(dibenzylideneacetone)dipalladium(0) (46.2 mg, 0.05 mmol) was added. The reaction mixture was stirred at 105°C in an oil bath 12h. The solution was diluted with EtOAc and washed with saturated NaHCO3 solution, brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was loaded on a 24g silica gel column and purified on a Teledyne Isco instrument, eluting with 10% to 40% ethyl acetate in heptane to provide (1S,4S)-tert-butyl 5-(4-(trifluoromethyl)pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (254 mg, 73.3 %) as a solid. 1H NMR (400MHz ,CHLOROFORM-d) d 8.26 (d, J = 5.5 Hz, 1 H), 6.75 (d, J = 5.1 Hz, 1 H), 6.48 (s, 1 H), 4.99 - 4.83 (m, 1 H), 4.76 - 4.52 (m, 1 H), 3.56 (t, J = 8.4 Hz, 1 H), 3.49 - 3.32 (m, 3 H), 2.04 - 1.91 (m, 2 H), 1.45 (d, J = 18.0 Hz, 9 H); MS m/z 344.2 [M+H]+ (ESI).

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CN=C(C=C1C(F)(F)F)Cl;amine:CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2, Reagents 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;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];Solvent:CC1=CC=CC=C1;Base:CC(C)(C)[O-].[Na+], and Products are 0:CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2C3=NC=CC(=C3)C(F)(F)F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A 2.0-5.0 mL microwave vial was charged with (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (150 mg, 0.76 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (47.1 mg, 0.08 mmol), Sodium tert-butoxide (87 mg, 0.91 mmol), 2-Chloro-4-(trifluoromethyl)pyridine (0.117 mL, 0.91 mmol) and and mixture of toluene (2.5 mL) and DMF (.5 mL). The reaction mixture was degassed for 10 minutes with nitrogen, and then Tris(dibenzylideneacetone)dipalladium(0) (34.6 mg, 0.04 mmol) was added. The reaction mixture was stirred at 120°C under microwave irradiation for 30 minutes. The solution was then irradiated for another 30 min at 120°C. The solution was diluted with EtOAc and washed with saturated NaHCO3 solution, brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was loaded on a 24g silica gel column and purified on a Teledyne Isco instrument, eluting with 10% to 40% ethyl acetate in heptane to provide (1S,4S)-tert-butyl 5-(4-(trifluoromethyl)pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (88 mg, 33.9 %) as a solid. MS m/z 344.2 [M+H]+ (ESI)

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC(=C(N=C1)Br)Cl;amine:CN1CC(CCC1=O)N, Reagents 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;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];Solvent:CC1=CC=CC=C1;Base:CC(C)(C)[O-].[Na+], and Products are 0:CN1CC(CCC1=O)NC2=C(C=CC=N2)Cl, please give me the reaction condition of this formula.

The condition of this chemical reaction is: In a 10 ml MW vial, Pd2((dba)3 (10.85 mg, 0.01 mmol), 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (14.56 mg, 0.02 mmol), sodium 2-methylpropan-2-olate (261 mg, 2.71 mmol), 5-amino-1-methylpiperidin-2-one (200 mg, 1.56 mmol) and 2-bromo-3-chloropyridine (300 mg, 1.56 mmol) mixed in toluene (3 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 for 1h then to rt for 2h. LC-MS 1h: 15% product. LC-MS o/n: 19% product. 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 20% to 100% of EtOAc in heptane over 20CV was used as mobile phase. The product was collected using the wavelength 307 and 241 nm. Product was not found in any of the fractions, reaction discarded.

Here is a chemical reaction formula: Reactants are:aryl halide:CC1=C(C=C(C=C1)[N+](=O)[O-])Br;amine:C1C(CO1)N.Cl, Reagents are:metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe];metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:CC1=C(C=C(C=C1)[N+](=O)[O-])NC2COC2, please give me the reaction condition of this formula.

The condition of this chemical reaction is: 2-bromo-1-methyl-4-nitrobenzene (864 mg, 4mmol), oxetan-3-amine hydrochloride (438 mg, 4 mmol), CS2CO3 (3910 mg, 12.00 mmol), palladium(II) acetate (44.9 mg, 0.20 mmol), (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t- butylphosphine (224 mg, 0.40 mmol) in 1,4-doxane was degased, inflated with Ar and heated at 90 oC for 5h. LCMS showed some product peak. Silica gel 2g was added to the mixture, evaporated all solvents in GeneVac. The sample was dry loaded for purification by ISCO (Hexane/EtOAc=100/10-100/50) N-(2-methyl-5-nitrophenyl)oxetan-3-amine (240 mg, 28.8 %) 1H NMR (400 MHz, CD2Cl2) d: 7.47 (dd, 1H), 7.14 (d, 1H), 6.98 (s, 1H), 4.99 (t, 2H), 4.63 (m, 1H), 4.46 (t, 2H), 4.20(m, 1H), 2.18 (s, 3H). LCMS: 209 [M+H]+.

Here is a chemical reaction formula: Reactants are:amine:C1=CC=C(C=C1)CN;aryl halide:C1=CC(=CC=C1NC2=NC=CC(=C2)Cl)F, Reagents are:Solvent:CC(=O)N(C)C;metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe];metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:CC(C)(C)[O-].[Na+], and Products are 0:C1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=C(C=C3)F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Phenylmethanamine (52.9 mg, 0.49 mmol), 4-chloro-N-(4-fluorophenyl)pyridin-2-amine (100 mg, 0.45 mmol) and sodium 2-methylpropan-2-olate (86 mg, 0.90 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 (29.9 mg, 0.05 mmol) and diacetoxypalladium (8.07 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-benzyl-N2-(4-fluorophenyl)pyridine-2,4-diamine (98 mg, 74.4 %) as an off-white solid.

Here is a chemical reaction formula: Reactants are:amine:COC1=C(C=CC(=C1)N2CCN(CC2)CCO)N;aryl halide:C1=CC2=C(C=NN2C=C1)C3=NC(=NC=C3Cl)Cl, Reagents are:Solvent:COCCOC;Base:C(=O)([O-])[O-].[Cs+].[Cs+];metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe];metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:COC1=C(C=CC(=C1)N2CCN(CC2)CCO)NC3=NC=C(C(=N3)C4=C5C=CC=CN5N=C4)Cl, please give me the reaction condition of this formula.

The condition of this chemical reaction is: 3-(2,5-dichloropyrimidin-4-yl)pyrazolo[1,5-a]pyridine (200 mg, 0.75 mmol), 2-(4-(4-amino-3-methoxyphenyl)piperazin-1-yl)ethanol (190 mg, 0.75 mmol), cesium carbonate (295 mg, 0.91 mmol), diacetoxypalladium (13.55 mg, 0.06 mmol) and (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T- BUTYLPHOSPHINE (41.8 mg, 0.08 mmol) were suspended in DME (5 mL) and sealed into a microwave tube. The reaction was degased, purged with nitrogen and heated to 140 °C over a period of 30 minutes in the microwave reactor. The reaction mixture was filtratet and the fitrate was evaporated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 5% methanol in dichloromethane. The solvent was evaporated to dryness to afford 2-(4-(4-(5-chloro-4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-ylamino)-3-methoxyphenyl)piperazin-1-yl)ethanol (60mg) 1H NMR 01570-55-03 as a red gum. The gum 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 2-(4-(4-(5-chloro-4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-ylamino)-3-methoxyphenyl)piperazin-1-yl)ethanol (40.0 mg, 11.05 %) as a yellow foam.

Here is a chemical reaction formula: Reactants are:amine:CC(C)(C)OC(=O)N1CCNCC1;aryl halide:C1=CC(=CC=C1C#N)Br, Reagents are:Base:CC(C)(C)[O-].[Na+];Solvent:C1CCOC1;metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C;metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=C(C=C2)C#N, please give me the reaction condition of this formula.

The condition of this chemical reaction is: To 4-bromobenzonitrile (.5 g, 2.75 mmol) dissolved in dry THF (10 mL) was added tert-butyl piperazine-1-carboxylate (0.512 g, 2.75 mmol), Sodium-t- butoxide (0.792 g, 8.24 mmol) and purged with N2 gas for 10 min followed by the addition of 2-(Dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1'-biphenyl (0.131 g, 0.27 mmol)and Palladium II acetate (0.062 g, 0.27 mmol). The contents were further purged with N2 gas for further 10 min and heated at 85 °C for 2 h. The reaction mass was concentrated and the reside diluted with water and extracted with ethyl acetate . The combined organic extracts were washed with brine solution and dried over anhydrous sodium sulphate. The organic layer was evaporated under reduced pressure to obtain the crude product which was purified by 60-120 mesh silica gel column chromatography using 25% Ethyl acetate : Hexanes mixture to obtain tert-butyl 4-(4-cyanophenyl)piperazine-1-carboxylate (0.650 g, 82 %) as a white solid. m/z (ES+), M+ = 288.4

Here is a chemical reaction formula: Reactants are:amine:CN1CCNCC1;aryl halide:COC1=CC(=CC(=C1)[N+](=O)[O-])Br, Reagents are:Solvent:CC1=CC=CC=C1;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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:CN1CCN(CC1)C2=CC(=CC(=C2)OC)[N+](=O)[O-], please give me the reaction condition of this formula.

The condition of this chemical reaction is: 1-bromo-3-methoxy-5-nitrobenzene (116 mg, 0.5 mmol), 1-methylpiperazine (167 µl, 1.50 mmol), Palladium(II) acetate (11.23 mg, 0.05 mmol), BINAP (31.1 mg, 0.05 mmol), Cs2CO3 (326 mg, 1.00 mmol) and PhCH3 (10 mL) were added to a 100ml rb flask and heated at 150 °C for 1h. LCMS showed rxn done with desired product formed. Rxn was filtered and concentrated. The residue was purified by Gilson (CH3CN/Water 0-50% + 0.1%TFA) to get the desired product 1-(3-methoxy-5-nitrophenyl)-4-methylpiperazine (130 mg, 71.2 %).

Here is a chemical reaction formula: Reactants are:aryl halide:COC1=C(C=CC(=C1)I)Br;amine:C1C(CO1)N, Reagents 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;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];Base:CC(C)(C)[O-].[Na+];Solvent:CC1=CC=CC=C1, and Products are 0:COC1=C(C=CC(=C1)NC2COC2)Br, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A solution of 1-bromo-4-iodo-2-methoxybenzene (0.60 g, 1.92 mmol) dissolved in toluene (15 mL) was treated with oxetan-3-amine (0.140 g, 1.92 mmol), SODIUM TERT-BUTOXIDE (0.221 g, 2.30 mmol), XANTPHOS (0.111 g, 0.19 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.044 g, 0.05 mmol) under nitrogen. The resulting mixture was stirred at 80 °C in a sealed tube for 2 hours. The reaction mixture was diluted with water (10 mL), and extracted with ethyl acetate (3x 20 mL). The organic was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution 0-30% EtOAc in Heptane. Pure fractions were evaporated to dryness to afford N-(4-bromo-3-methoxyphenyl)oxetan-3-amine (0.177 g, 35.8 %) as a beige solid.

Here is a chemical reaction formula: Reactants are:aryl halide:COC1=NC(=NC=C1Br)I;amine:CCNC1=CC=CC=C1, Reagents are:Solvent:CC1=CC=CC=C1;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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:CCC(C)(C)[O-].[Na+], and Products are 0:CCN(C1=CC=CC=C1)C2=NC=C(C(=N2)OC)Br, please give me the reaction condition of this formula.

The condition of this chemical reaction is: 5-bromo-2-iodo-4-methoxypyrimidine (0.086 g, 0.27 mmol), diacetoxypalladium (2.78 mg, 0.01 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) - XantPhos (7.16 mg, 0.01 mmol) and sodium 2-methylbutan-2-olate (0.055 g, 0.50 mmol) and di((3S,5S,7S)-adamantan-1-yl)(butyl)phosphine (8.88 mg, 0.02 mmol) were added to a micro vial. Then N-ethylaniline (0.031 mL, 0.25 mmol) in toluene (1.5 mL) was added to the reaction mixture. The vial was sealed and evacuated and flushed with nitrogen and then stirred at 100°C o/n. LC/MS showed product formation. The reaction mixture was cooled to rt and then filtered over celite. The crude product was diluted with 25 ml of DCM and then washed with sat. NaHCO3 followed by brine. The organic phase was dried over a phase separator and then concentrated to dryness. **No LC/MS data due to database failure over three months and was only saved locally on LC/MS computer and pdf-files seems to be deleted on machine. Not used in further reactions.**

Here is a chemical reaction formula: Reactants are:aryl halide:COC1=NC(=NC=C1Br)I;amine:CCNC1=CC=CC=C1, Reagents are:Base:CCC(C)(C)[O-].[Na+];Solvent:CC1=CC=CC=C1;metal and ligand:CCCCP(C12CC3CC(C1)CC(C3)C2)C45CC6CC(C4)CC(C6)C5;metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:CCN(C1=CC=CC=C1)C2=NC=C(C(=N2)OC)Br, please give me the reaction condition of this formula.

The condition of this chemical reaction is: 5-bromo-2-iodo-4-methoxypyrimidine (0.086 g, 0.27 mmol), diacetoxypalladium (2.78 mg, 0.01 mmol), di((3S,5S,7S)-adamantan-1-yl)(butyl)phosphine (8.88 mg, 0.02 mmol) and sodium 2-methylbutan-2-olate (0.033 g, 0.30 mmol) were added to a micro vial. Then N-ethylaniline (0.031 mL, 0.25 mmol) in toluene (1.5 mL) was added to the reaction mixture. The vial was sealed and evacuated and flushed with nitrogen and then stirred at 60°C o/n. LC/MS showed product formation. The reaction mixture was cooled to rt and then filtered over celite. The crude product was diluted with 25 ml of DCM and then washed with sat. NaHCO3 followed by brine. The organic phase was dried over a phase separator and then concentrated to dryness. **No LC/MS data due to database failure over three months and was only saved locally on LC/MS computer and pdf-files seems to be deleted on machine. Not used in further reactions.**

Here is a chemical reaction formula: Reactants are:aryl halide:CC(C)(C)OC(=O)NC1=C(C=CC(=C1)Br)Cl;amine:C1CNCCN1, Reagents are:Solvent:CC1=CC=CC=C1;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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:CC(C)(C)OC(=O)NC1=C(C=CC(=C1)N2CCNCC2)Cl, please give me the reaction condition of this formula.

The condition of this chemical reaction is: palladium(II) acetate (0.110 g, 0.49 mmol), BINAP (0.244 g, 0.39 mmol) and CS2CO3 (1.594 g, 4.89 mmol) were added to a mixture of [Reactants] and piperazine (2.76 g, 32.10 mmol) in toluene (10 mL), The suspension were heated to 110 °C for 16 hours, LCMS showed product mass [M+1]:312.0 at retention time RT=1.69 min (polar short purity method). Workup reaction by additional of water (10mL), extracted with EtOAc (3x20 mL), washed with brine, dried with Na2SO4, evaporated off solvent to give a residue, which was purified by isco chromatographer, eluting with 0-10% MeOH in DCM to give as a yellow solid. LCMS confirmed the target compound.

Here is a chemical reaction formula: Reactants are:aryl halide:CC1=C(C=C(C=N1)[N+](=O)[O-])Br;amine:C1=CC(=CN=C1)C2=NC(=NC=C2)N, Reagents are:Solvent:CC1=CC=CC=C1;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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:CC1=C(C=C(C=N1)[N+](=O)[O-])NC2=NC=CC(=N2)C3=CN=CC=C3, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Palladium(II) acetate (65.3 mg, 0.29 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (336 mg, 0.58 mmol) were mixed together in a reaction vessel and evacuated and purged with nitrogen 3 times. Toluene (35 ml) was added and the resulting mixture was heated to to 50°C for 45 minutes. To this mixture was added 3-bromo-2-methyl-5-nitropyridine (694 mg, 3.20 mmol), then 4-(pyridin-3-yl)pyrimidin-2-amine (500 mg, 2.91 mmol) and cesium carbonate (1421 mg, 4.36 mmol), and the resulting mixture heated at 90 °C for 16 hours. The reaction mixture was cooled to RT, 50ml EtOAc was added and the mixture was filtered. The filtrate was concentrated, diluted with EtOAc (200 mL), and washed sequentially with water (150 mL) and saturated brine (150 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product, ~2g brown wet solid. The crude product was purified by flash silica chromatography, elution gradient 0 to 4% MeOH in DCM. Pure fractions eluting at 3% were evaporated to dryness to afford N-(2-methyl-5-nitropyridin-3-yl)-4-(pyridin-3-yl)pyrimidin-2-amine (169 mg, 18.86 %) as a colourless solid. .

Here is a chemical reaction formula: Reactants are:amine:C1=CC(=CN=C1)C2=NC(=NC=C2)N;aryl halide:CC1=C(C=C(C=N1)[N+](=O)[O-])Br, Reagents are:Solvent:CC1=CC=CC=C1;Base:C(=O)([O-])[O-].[Cs+].[Cs+];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;metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:CC1=C(C=C(C=N1)[N+](=O)[O-])NC2=NC=CC(=N2)C3=CN=CC=C3, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Palladium(II) acetate (65.3 mg, 0.29 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (336 mg, 0.58 mmol) were mixed together in a reaction vessel and evacuated and purged with nitrogen 3 times. Toluene (35 ml) was added and the resulting mixture was heated to to 50°C for 45 minutes, then cooled to r.t. To this mixture at r.t was added 3-bromo-2-methyl-5-nitropyridine (694 mg, 3.20 mmol), then 4-(pyridin-3-yl)pyrimidin-2-amine (500 mg, 2.91 mmol) and cesium carbonate (1421 mg, 4.36 mmol), and the resulting mixture heated at 90 °C for 16 hours under N2. The reaction mixture was cooled to RT, 150ml EtOAc was added and the mixture was filtered. The filtrate was concentrated, diluted with EtOAc (500 mL), and washed sequentially with water (300 mL) and saturated brine (150 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product, ~2g brown wet solid. The crude product was purified by flash silica chromatography, elution gradient 0 to 4% MeOH in DCM. Pure fractions eluting at 3% were evaporated to dryness to afford N-(2-methyl-5-nitropyridin-3-yl)-4-(pyridin-3-yl)pyrimidin-2-amine (169 mg, 18.86 %) as a cream solid.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC(=NC(=C1)Cl)Cl;amine:C1=CC=C(C=C1)N, Reagents 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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Solvent:CC1=CC=CC=C1;Base:C(=O)([O-])[O-].[K+].[K+], and Products are 0:C1=CC=C(C=C1)NC2=NC(=CC=C2)Cl, please give me the reaction condition of this formula.

The condition of this chemical reaction is: 2,6-dichloropyridine (228 mg, 1.54 mmol) was dissolved in toluene (7.5 ml) and diacetoxypalladium (6 mg, 0.03 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (19 mg, 0.03 mmol), aniline (0.170 ml, 1.87 mmol) and potassium carbonate (583 mg, 4.22 mmol) were added added. The reaction mixture was sparged with notrogen for 3-4 minutes before being sealed into a microwave tube and heated to 160 °C over ~3 minutes, before holding at that temperature for 30 minutes. After cooling to ambient temperature the reaction mixture was diluted to ~40 mL with ethyl acetate and insoluble material removed by filtration. The filtrate was evaporated and purification attempted by flash silica chromatography, elution gradient 0 to 50% EtOAc in heptane. Product containing fractions were evaporated to dryness to afford 6-chloro-N-phenylpyridin-2-amine (167 mg, 53.0 %) as a waxy pale yellow solid

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;amine:C1=C2C(=CC(=C1F)F)NC(=O)C=C2Cl, Reagents 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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Solvent:CC1=CC=CC=C1;Base:C(=O)([O-])[O-].[Cs+].[Cs+], and 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 formula.

The condition of this chemical reaction is: In a 25ml Biotage microwave vial, 4-chloro-6,7-difluoroquinolin-2(1H)-one (0.175 g, 0.81 mmol), ((2S,4R)-4-amino-2-methylpiperidin-1-yl)(5-chloro-1-methyl-1H-pyrazol-4-yl)methanone (0.208 g, 0.81 mmol) ,racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.051 g, 0.08 mmol), Cesium carbonate (0.793 g, 2.44 mmol), Palladium (II) acetate (0.018 g, 0.08 mmol) were taken were taken in toluene (10 mL) to give brown suspension. The reaction mass was subjected to microwave irradiation at 140 oC for 1 hour. The reaction ws monitored by LCMS, indicated required product formation. Workup: The reaction mixture was concentrated to dryness and purified by silica gel column chromatography using 0 to 20% Methanol in DCM and then purified by reverse phase chromatography to obtain 4-(((2S,4R)-1-(5-chloro-1-methyl-1H-pyrazole-4-carbonyl)-2-methylpiperidin-4-yl)amino)-6,7-difluoroquinolin-2(1H)-one (0.030 g, 8.48 %) as white solid. The compound was submitted for biological testing.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC(=C(N=C1)Br)Cl;amine:CC1(COC1)CN, Reagents are:Solvent:CC1=CC=CC=C1;Base:CC(C)(C)[O-].[Na+];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;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], and Products are 0:CC1(COC1)CNC2=C(C=CC=N2)Cl, please give me the reaction condition of this formula.

The condition of this chemical reaction is: In a 5 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), (3-methyloxetan-3-yl)methanamine (126 mg, 1.25 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 for 1h then to rt for 2h. LC-MS: 61% product, 28% sm left. The reaction was cooled to rt and the solvent was evaporated. The residue was purified by automated flash chromatography on a 25g column. A gradient from 5% to 50% of EtOAc in heptane over 15CV was used as mobile phase. The product was collected using the wavelength 315 nm, relevant fractions pooled and evaporated to give 27 mg suryp. LC-MS: M+1=213 found. 1H-NMR: OK, traces of sm and solvents left. 1H NMR (400 MHz, CDCl3) d 1.37 (s, 3H), 3.70 (d, 2H), 4.42 (d, 2H), 4.58 (d, 2H), 5.25 (s, 1H), 6.53 (dd, 1H), 7.44 (dd, 1H), 8.00 (dd, 1H). Expected Number of Hs: 13 Assigned Hs: 13.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC(=CN=C1)Br;amine:CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2, Reagents 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;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];Solvent:CC1=CC=CC=C1;Base:CC(C)(C)[O-].[Na+], and Products are 0:CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2C3=CN=CC=C3, please give me the reaction condition of this formula.

The condition of this chemical reaction is: TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.055 g, 0.06 mmol) and rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.075 g, 0.12 mmol) were mixed together and evacuated and purged with nitrogen 3 times. toluene (29.7 ml) was added and the resulting mixture heated to 90°C for 10 minutes then cooled to room temperature. In a second reaction vessel was mixed sodium tert-butoxide (0.465 g, 4.84 mmol), 3-bromopyridine (0.321 ml, 3.33 mmol) and (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.601 g, 3.03 mmol) and toluene (29.7 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 85 °C for 64 hours. The reaction mixture was cooled to RT and filtered through celite and concentrated to give an orange solid. The crude product was purified by flash silica chromatography, elution gradient 30 to 50% EtOAc in heptane. Then 100% MeOH. Pure fractions were evaporated to dryness to afford (1S,4S)-tert-butyl 5-(pyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.823 g, 99 %) as a pale yellow dry film.

Here is a chemical reaction formula: Reactants are:aryl halide:CC1=C(C(=CC=C1)C)C(=O)NC(C2=CC(=CC=C2)Br)C34CCC(N3C)CC4;amine:C1COCCN1, Reagents are:Solvent:CC1=CC=CC=C1;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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:CC(C)(C)[O-].[Na+], and Products are 0:CC1=C(C(=CC=C1)C)C(=O)NC(C2=CC(=CC=C2)N3CCOCC3)C45CCC(N4C)CC5, please give me the reaction condition of this formula.

The condition of this chemical reaction is: To a suspension of N-((3-bromophenyl)(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)methyl)-2,6-dimethylbenzamide (0.040 g, 0.09 mmol), MORPHOLINE (8.97 µL, 0.10 mmol), BINAP (5.83 mg, 9.36 µmol), and sodium tert-butoxide (0.013 g, 0.14 mmol) in toluene (2 mL) was added palladium(II) acetate (1.051 mg, 4.68 µmol). Nitrogen was passed through the solution for 15 min prior to being heated at 80 °C overnight. Crude LC shows starting material still present. Heated to 110oC for 2 days. Reaqction no longer progressing. Reaction mixture was concentrated in vacuo. Material was diluted with ethyl acetate, filtered thru celite and concentrated in vacuo. Submitted to purification group (52 mg in 1.6 mL DMSO). Received back dried- down fractions. Diluted with DCM, combined and concentrated to afford 2,6-dimethyl-N-((7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)(3-morpholinophenyl)methyl)benzamide (7.30 mg, 17.99 %) Submitted 4.5 mg Vial # 26243972 (TWOC): 7.0545 g

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl;amine:COC1=CC=C(C=C1)CN, Reagents are:Solvent:CC(=O)N(C)C;Base:CC(C)(C)[O-].[Na+];metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe];metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:COC1=CC=C(C=C1)CNC2=CC(=NC=C2)NC3=CC=CC=C3, please give me the reaction condition of this formula.

The condition of this chemical reaction is: (4-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-(4-methoxybenzyl)-N2-phenylpyridine-2,4-diamine (101 mg, 67.7 %) as a white solid.

Here is a chemical reaction formula: Reactants are:amine:C1C2=CC=CC=C2CN1;aryl halide:C1=CC(=CC=C1Br)I, Reagents are:Base:CC(C)(C)[O-].[Na+];Solvent:CC1=CC=CC=C1;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;metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:C1C2=CC=CC=C2CN1C3=CC=C(C=C3)Br, please give me the reaction condition of this formula.

The condition of this chemical reaction is: palladium(II) acetate (0.112 g, 0.50 mmol) and XANTPHOS (0.288 g, 0.50 mmol) were added to a degassed solution of isoindoline (0.566 ml, 4.98 mmol), 1-bromo-4-iodobenzene (1.41 g, 4.98 mmol) and SODIUM TERT-BUTOXIDE (1.197 g, 12.46 mmol) in toluene (49.3 ml) under nitrogen. The resulting solution was stirred at 100 °C for 18 hours. The reaction mixture was allowed to cool to RT and was partitioned between EtOAc and H2O, filtered and the organic layer separated and dried over MgSO4, filtered and evaporated to dryness to give crude product. The crude product preabsorbed onto SiO2 and was purified by flash silica (40g, grace) chromatography, elution gradient 0 to 10% DCM in heptane. Pure fractions were evaporated to dryness to afford 2-(4-bromophenyl)isoindoline (0.660 g, 48.3 %) as an orange solid.

Here is a chemical reaction formula: Reactants are:amine:CN1CC(C1)N.Cl;aryl halide:C1=CC(=C(N=C1)Br)Cl, Reagents 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;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];Solvent:CC1=CC=CC=C1;Base:CC(C)(C)[O-].[Na+], and Products are 0:CN1CC(C1)NC2=C(C=CC=N2)Cl, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Pd2(dba)3 (0.018 g, 0.02 mmol), 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (0.024 g, 0.04 mmol) and toluene (4 mL) was added to a flask. 2-bromo-3-chloropyridine (0.5 g, 2.60 mmol), 1-methylazetidin-3-amine hydrochloride (0.414 g, 3.38 mmol) and sodium 2-methylpropan-2-olate (0.624 g, 6.50 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 for 2h, then to rt over night. The reaction was cooled to rt and the solvent was evaporated. The residue was purified by automated flash chromatography on a 100g column. A gradient from 10% to 100% of EtOAc (with 2% TEA) in heptane over 25CV was used as mobile phase. The product was collected using the wavelength 243 and 308 nm. No product found in any fractions. Reaction discarded.

Here is a chemical reaction formula: Reactants are:amine:CC(C)(C)OC(=O)N1CCNCC1;aryl halide:COC(=O)C1=CC(=CC(=C1)Br)F, Reagents are:Base:CC(C)(C)[O-].[Na+];Solvent:C1CCOC1;metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C;metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=CC(=C2)C(=O)O)F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: To methyl 3-bromo-5-fluorobenzoate (1.5 g, 6.44 mmol) dissolved in dry THF (20 mL) was added tert-butyl piperazine-1-carboxylate (1.199 g, 6.44 mmol), Sodium-t-butoxide (1.856 g, 19.31 mmol) and purged with N2 gas for 10 min followed by the addition of2-(Dicyclohexylphosphino)-2',4',6'-tri-i- propyl-1,1'-biphenyl (0.307 g, 0.64 mmol), Palladium II acetate (0.145 g, 0.64 mmol) . The contents were further purged with N2 gas for further 10 min and heated at 85 °C for overnight. The reaction mass was concentrated and the reside diluted with water and extracted with ethyl acetate . The combined organic extracts were washed with brine solution and dried over anhydrous sodium sulphate. The organic layer was evaporated under reduced pressure to obtain the crude product which was purified by 60-120 mesh silica gel column chromatography using 25% Ethyl acetate ; hexanes mixture to obtain 3-(4-(tert- butoxycarbonyl)piperazin-1-yl)-5-fluorobenzoic acid (1.500 g, 71.8 %) an oil. m/z (ES-), M- = 323

Here is a chemical reaction formula: Reactants are:amine:CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C1)C(=O)N;aryl halide:CC1(CC2=C(C=NN2C1)C3=CC(=NC=C3F)Cl)C, Reagents 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;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];Solvent:C1COCCO1;Base:C(=O)([O-])[O-].[Cs+].[Cs+], and 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 formula.

The condition of this chemical reaction is: Tetrakis(triphenylphosphine)palladium(0) (0.094 g, 0.08 mmol) was added to Racemic tert-butyl ((1R,3R)-3-carbamoylcyclohexyl)carbamate (0.235 g, 0.97 mmol),3-(2-chloro-5-fluoropyridin-4-yl)-5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (0.215 g, 0.81 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (0.094 g, 0.16 mmol) and cesium carbonate (0.791 g, 2.43 mmol) in 1,4-dioxane (6 mL) and water (1.200 mL). The resulting suspension was degassed for 10 minutes under nitrogen and then stirred at 100 °C for 48 hours. LCMS is complete, it needs this long. The mixture was cooled, diluted with water (40 ml), and extracted with EtOAc (3 x 20 ml). The combined organics were evaporated to crude material. 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 Racemic tert-butyl ((1R,3R)-3-((4-(5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-5-fluoropyridin-2-yl)carbamoyl)cyclohexyl)carbamate (0.322 g, 84 %) as a white foam.

Here is a chemical reaction formula: Reactants are:amine:CC(C)(C)OC(=O)N1CCNCC1;aryl halide:CCOC1=C(C=C(C=C1)Br)Cl, Reagents 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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:C(=O)([O-])[O-].[Cs+].[Cs+];Solvent:CC1=CC=CC=C1, and Products are 0:CCOC1=C(C=C(C=C1)N2CCN(CC2)C(=O)OC(C)(C)C)Cl, please give me the reaction condition of this formula.

The condition of this chemical reaction is: In a 50 mL round-bottomed flask, PALLADIUM ACETATE (0.014 g, 0.06 mmol) was treated with BINAP (0.079 g, 0.13 mmol) under nitrogen in degassed Toluene (12.74 ml). The reaction was heated to 80 °C and was stirred for 10 min. To the flask was then added tert-butyl piperazine-1-carboxylate (0.237 g, 1.27 mmol), cesium carbonate (0.208 g, 0.64 mmol), potassium carbonate (0.176 g, 1.27 mmol), and 18-CROWN-6 (0.034 g, 0.13 mmol). The reaction was then treated with 4-bromo-2-chloro-1-ethoxybenzene (0.300 g, 1.27 mmol) and was allowed to stir at 80°C 5 h. **LCMS High pH:** No reaction observed

Here is a chemical reaction formula: Reactants are:aryl halide:COC1=C(C=CC(=C1)I)Br;amine:CN(C)CCN, Reagents 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;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];Solvent:CC1=CC=CC=C1;Base:CC(C)(C)[O-].[Na+], and Products are 0:CN(C)CCNC1=CC(=C(C=C1)Br)OC, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A solution of 1-bromo-4-iodo-2-methoxybenzene (0.63 g, 2.01 mmol) dissolved in toluene (15.73 ml) was treated with N1,N1-dimethylethane-1,2-diamine (0.177 g, 2.01 mmol), SODIUM TERT-BUTOXIDE (0.232 g, 2.42 mmol), XANTPHOS (0.116 g, 0.20 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.046 g, 0.05 mmol) under nitrogen. The resulting mixture was stirred at 80 °C in a sealed tube for 2 hours. The reaction mixture was diluted with water (200 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 flash silica chromatography, elution 0-10% methanol in dcm. Pure fractions were evaporated to dryness to afford N1-(4-bromo-3-methoxyphenyl)-N2,N2-dimethylethane-1,2-diamine (0.251 g, 45.6 %) as a brown oil.

Here is a chemical reaction formula: Reactants are:aryl halide:CNC(=O)C1=CC(=NC(=C1)Cl)Cl;amine:C1=CC=C(C=C1)N, Reagents 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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Solvent:CC1=CC=CC=C1;Base:CC(C)(C)[O-].[Na+], and Products are 0:CNC(=O)C1=CC(=NC(=C1)Cl)NC2=CC=CC=C2, please give me the reaction condition of this formula.

The condition of this chemical reaction is: SODIUM TERT-BUTOXIDE (0.984 g, 10.24 mmol) was added to 2,6-dichloro-N- methylisonicotinamide (1.5 g, 7.32 mmol), ANILINE (0.667 mL, 7.32 mmol), PALLADIUM(II) ACETATE (0.016 g, 0.07 mmol) and XANTPHOS (0.127 g, 0.22 mmol) in toluene (30 mL) under nitrogen. The resulting mixture was stirred at 80 °C for 4 hours. The reaction mixture was evaporated to dryness and redissolved in EtOAc (100 mL), and washed sequentially with water (2 x 50 mL) and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and preadsorbed onto silica. The crude product was purified by flash silica chromatography, elution gradient 30 to 80% EtOAc in heptane. Pure fractions were evaporated to dryness to afford 2-chloro-N- methyl-6-(phenylamino)isonicotinamide (1.012 g, 52.9 %) as a cream solid.

Here is a chemical reaction formula: Reactants are:amine:C1=CC(=CC(=C1)F)CN;aryl halide:C1=CC=C(C=C1)NC2=NC=CC(=C2)Cl, Reagents are:metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe];metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:CC(C)(C)[O-].[Na+];Solvent:CC(=O)N(C)C, and Products are 0:C1=CC=C(C=C1)NC2=NC=CC(=C2)NCC3=CC(=CC=C3)F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: (3-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-(3-fluorobenzyl)-N2-phenylpyridine-2,4-diamine (84 mg, 58.6 %) as an off-white solid.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC(=CC=C1Br)I;amine:C1CCN(CC1)C2CCNCC2, Reagents are:Base:CC(C)(C)[O-].[Na+];Solvent:CC1=CC=CC=C1;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;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], and Products are 0:C1CCN(CC1)C2CCN(CC2)C3=CC=C(C=C3)Br, please give me the reaction condition of this formula.

The condition of this chemical reaction is: TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.162 g, 0.18 mmol) was added to 1,4'-bipiperidine (0.595 g, 3.53 mmol), 1-bromo-4-iodobenzene (1.000 g, 3.53 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.205 g, 0.35 mmol) and sodium 2-methylpropan-2-olate (0.408 g, 4.24 mmol) in toluene (10 mL). The resulting mixture was degassed again and was stirred at 80 °C for 18 hours under nitrogen. The reaction mixture was cooled to room temperature and filtered then the filtrate was diluted with EtOAc (50 mL), and washed sequentially with water (50 mL), water (50 mL), and saturated brine (50 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 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford 1'-(4-bromophenyl)-1,4'-bipiperidine (0.736 g, 64.4 %) as a pale brown oil.

Here is a chemical reaction formula: Reactants are:aryl halide:CCOC1=C(C=C(C=C1)Br)OC;amine:C[C@@H]1CNCCN1C(=O)OC(C)(C)C, Reagents are:Solvent:CC1=CC=CC=C1;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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:CC(C)(C)[O-].[Na+], and Products are 0:CCOC1=C(C=C(C=C1)N2CCN[C@@H](C2)C)OC, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Palladium(II) acetate (0.049 g, 0.22 mmol)and (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.108 g, 0.17 mmol) were added to 4-bromo-1-ethoxy-2-methoxybenzene (1 g, 4.33 mmol),(R)-1-N-Boc-2-methyl piperazine (0.867 g, 4.33 mmol) and Sodium tert- butoxide (0.624 g, 6.49 mmol) in anhydrous Toluene (20 mL) under argon. 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 (R)-1-(4-ethoxy-3-methoxyphenyl)-3-methylpiperazine (0.550 g, 50.8 %) as a yellow gum.

Here is a chemical reaction formula: Reactants are:amine:CC(C)(C)OC(=O)N1CCNCC1;aryl halide:CN(C)C1=CC=CC=C1Br, Reagents are:Solvent:CC1=CC=CC=C1;metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:CC(C)(C)[O-].[Na+], and Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC=C2N(C)C, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Palladium (II) acetate (67.3 mg, 0.30 mmol) and 2-dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl (280 mg, 0.60 mmol) were dissolved in toluene (7 mL) and purged with nitrogen. The mixture was warmed to 50°C for 15 mins. In a separate vessel, were mixed 2-bromo-N,N-dimethylaniline (600 mg, 3.00 mmol), tert-butyl piperazine-1-carboxylate (559 mg, 3.00 mmol) and sodium-t- butoxide (432 mg, 4.50 mmol) in toluene (8 mL). The mixture was degassed and purged with nitrogen. The catalyst solution was added and the resulting mixture heated at 100°C overnight. The reaction mixture was filtered through celite, washing with MeOH/EtOAc. The filtrate was concentrated and purified by flash silica chromatography, elution gradient 0 to 70% EtOAc in heptane. Pure fractions were evaporated to dryness to afford tert-butyl 4-(2-(dimethylamino)phenyl)piperazine-1-carboxylate (293 mg, 32.0 %) as a colourless gum. Difficult column; three spots with same Rf, but clearly different retention times. Product present, but purity low. Carry through and de-BOC. See if can purify at that stage.

Here is a chemical reaction formula: Reactants are:aryl halide:COC1=CC=CC=C1Cl;amine:CC(C)(C)OC(=O)N1CCNCC1, Reagents are:Base:CC(C)(C)[O-].[Na+];Solvent:CC1=CC=CC=C1;metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4;metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC=C2OC, please give me the reaction condition of this formula.

The condition of this chemical reaction is: RuPhos (32.7 mg, 0.07 mmol) and palladium (II) acetate (15.75 mg, 0.07 mmol) were suspended in toluene (1 mL) at ambient temperature. The mixture was degassed and purged with nitrogen several times and warmed to 50°C for 20 mins. In a separate vessel were mixed 1-chloro-2-methoxybenzene (100 mg, 0.70 mmol), tert-butyl piperazine-1-carboxylate (131 mg, 0.70 mmol), sodium tertbutoxide (101 mg, 1.05 mmol) and toluene (2 mL). The suspension was degassed and purged with nitrogen then warmed to 50°C. The solution of catalyst was added to the reaction vessel and the resulting mixture was degassed and purged with nitrogen. The reaction was heated to 110°C (ext T) under nitrogen for 6 hours then allowed to cool to ambient temperature overnight. The reaction mixture was filtered and concentrated and the crude material purified by flash silica chromatography, elution gradient 20 to 60% EtOAc in heptane. Pure fractions were evaporated to dryness to afford tert-butyl 4-(2-methoxyphenyl)piperazine-1-carboxylate (23.00 mg, 11.22 %) as a colourless dry film. Yield not good....if this route followed maybe try different catalyst - pepsi?

Here is a chemical reaction formula: Reactants are:amine:C[C@H]1CNCCN1C;aryl halide:CC1=CC(=NC=C1C2=CC=C(C=C2)C3=NC4=C(C=CC=C4C(=O)N3)CO)Cl, Reagents are:metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4;metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)(C)OC.C1=CC=C([C-]=C1)CCN.Cl[Pd+];Base:CC(C)(C)[O-].[Na+];Solvent:C1COCCO1, and Products are 0:C[C@H]1CN(CCN1C)C2=NC=C(C(=C2)C)C3=CC=C(C=C3)C4=NC5=C(C=CC=C5C(=O)N4)CO, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A mixture of CHLORO(2-DICYCLOHEXYLPHOSPHINO-2',6'-DI-I- PROPOXY-1,1'-BIPHENYL)[2-(2-AMINOETHYLPHENYL)]PALLADIUM(II), METHYL-T- BUTYLETHER ADDUCT (Ru Phos Pd cycle) (43.2 mgs, 0.1eq), sodium tert-butoxide (229 mg, 2.38 mmol), 2-(4-(6-chloro-4-methylpyridin-3-yl)phenyl)-8-(hydroxymethyl)quinazolin-4(3H)-one (250 mg, 0.53 mmol) , (S)-1,2-dimethylpiperazine (198 mg, 1.06 mmol) in dioxane (25ml) was stirred at 105°C for 1hr, LCMS only detected a small peak as product. 2 more equivalent of sodium tert-butoxide was added to the mixture and stirred for overnight under N2, LCMS indicated major peak as starting material; another batch of Ru phos pd cycle was added to the mixture, and the mixture was stirred at 120°C for 1.5hrs. LCMS indicated the completion of reaction. The solvent was removed by concentration, taken into 2ml of DMSO, filtered, the filtrate was purified with reverse phase chromatography column (eluted with 5% to 50% 0.1%TFA in ACN/0.1%TFA in water) and repurified with basic condition (eluted with 5% to 95% ACN/10MM ammonium acetate and 10MM ACN in water), still not pure enough for submission. Repurified again by analytical group, to yield (S)-2-(4-(6-(3,4-dimethylpiperazin-1-yl)-4-methylpyridin-3-yl)phenyl)-8-(hydroxymethyl)quinazolin-4(3H)-one (64.0 mg, 26.5 %) as a light yellow solid.

Here is a chemical reaction formula: Reactants are:aryl halide:CC1=CC(=NC=C1C2=CC=C(C=C2)C3=NC4=C(C=CC=C4C(=O)N3)CO)Cl;amine:C[C@H]1CNCCN1C, Reagents are:Base:CC(C)(C)[O-].[Na+];Solvent:C1COCCO1;metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4;metal and ligand:CC(C)OC1=C(C(=CC=C1)OC(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4.CC(C)(C)OC.C1=CC=C([C-]=C1)CCN.Cl[Pd+], and Products are 0:C[C@H]1CN(CCN1C)C2=NC=C(C(=C2)C)C3=CC=C(C=C3)C4=NC5=C(C=CC=C5C(=O)N4)CO, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A mixture of CHLORO(2-DICYCLOHEXYLPHOSPHINO-2',6'-DI-I- PROPOXY-1,1'-BIPHENYL)[2-(2-AMINOETHYLPHENYL)]PALLADIUM(II), METHYL-T- BUTYLETHER ADDUCT (Ru Phos Pd cycle) (69.2 mgs, 0.2eq), sodium tert-butoxide (244 mg, 2.54 mmol) ,2-(4-(6-chloro-4-methylpyridin-3-yl)phenyl)-8-(hydroxymethyl)quinazolin-4(3H)-one (200 mg, 0.42 mmol) , (S)-1,2-dimethylpiperazine (198 mg, 1.06 mmol) in dioxane (20ml) was stirred at 115°C for 1hr, LCMS indicated the completion of reaction. The solid was filtered off through a pad of celite, washed with DCM. The solvent of the filtrate was removed by concentration, taken into 2ml of DMSO, purified with reverse phase chromatography column (eluted with 5% to 50% 0.1%TFA in ACN/0.1%TFA in water), the fractions were combined and lyphlized, to yield 117mgs of product. LCMS indicated 9% of TFA coupled side product. The solid was taken into 10ml sat. NaHCO3 aq, sonicated, until the disapearance of the side product, filtered, washed with water, dried to yield (S)-2-(4-(6-(3,4-dimethylpiperazin-1-yl)-4-methylpyridin-3-yl)phenyl)-8-(hydroxymethyl)quinazolin-4(3H)-one (67.0 mg, 34.7 %) as a yellow solid.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC(=NC=C1I)Br;amine:C1COCCN1, Reagents are:Base:CC(C)(C)[O-].[Na+];Solvent:CC1=CC=CC=C1;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;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], and Products are 0:C1COCCN1C2=CN=C(C=C2)Br, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Pd2(dba)3 (0.564 g, 0.62 mmol) was added to 2-bromo-5-iodopyridine (5.00 g, 17.61 mmol), morpholine (1.541 mL, 17.61 mmol), sodium tert-butoxide (4.23 g, 44.03 mmol) and Xantphos (1.019 g, 1.76 mmol) in toluene (200 mL) at 20°C. The resulting solution was stirred at r.t. for 3 days (as the reaction was started on a Friday). Complete. The reaction mixture was diluted with EtOAc (100 mL), and washed sequentially with water (100 mL) and saturated brine (100 mL). The organic layer was dried with MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% (EtOAc:MeOH - 10:1) in heptane. Pure fractions were evaporated to dryness LCMS indicated some di-substituted product present. Triturated in heptane:EtOAc, filtered and dried to afford 4-(6-bromopyridin-3-yl)morpholine (2.400 g, 56.1 %) as a beige solid.

Here is a chemical reaction formula: Reactants are:aryl halide:CC1(C2=NC(=C(N2CCN1C(=O)CNC(=O)OC(C)(C)C)Br)C3=CC=C(C=C3)F)C;amine:C1=CC(=CC=C1N)F, Reagents 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;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];Solvent:C1COCCO1;Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:CC1(C2=NC(=C(N2CCN1C(=O)CNC(=O)OC(C)(C)C)NC3=CC=C(C=C3)F)C4=CC=C(C=C4)F)C, please give me the reaction condition of this formula.

The condition of this chemical reaction is: In a microwave vial, cesium carbonate (135 mg, 0.42 mmol), 4-fluoroaniline (92 mg, 0.83 mmol), tris(dibenzylideneacetone)dipalladium(0) (19.02 mg, 0.02 mmol), Xantphos (24.04 mg, 0.04 mmol) and dry 1,4-dioxane (6 mL) were stirred for 5 minutes at room temperature. tert-butyl (2-(3-bromo-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)-2-oxoethyl)carbamate (200 mg, 0.42 mmol) was added to the reaction mixture after which the reaction mixture was degassed for 15 mins and then stirred at 120 °C under N2 for 20 h. The reaction was monitored by LCMS. The profile showed formation of title product. The reaction mixture was filtered through a pad opf celite and the filtrate was concentrated to give a residue. The residue was purified by silica gel followed by reverse phase HPLC to give tert-butyl (2-(2-(4-fluorophenyl)-3-((4-fluorophenyl)amino)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)-2-oxoethyl)carbamate (177 mg, 83 %) as a white solid. Conclusion: The product was used for the next step.

Here is a chemical reaction formula: Reactants are:amine:COC1=CC=CC(=C1)N;aryl halide:C1=CC(=CC(=C1)Br)C(F)(F)F, Reagents are:Solvent:COC1=CC=CC=C1;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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:CC(C)(C)[O-].[Na+], and Products are 0:COC1=CC=CC(=C1)NC2=CC=CC(=C2)C(F)(F)F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: PdOAc2 (8 mg, 0.04 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (40 mg, 0.07 mmol) were added to a dried vial. The vial was caped with a septa-cap and inerted with nitrogen. Degassed anisole (2 mL)was added and the catalyst mixture was heated to 50ºC for 30 minutes, then cooled down to rt. A dry 2ml microwave vial was charged with sodium 2-methylpropan-2-olate (52 mg, 0.54 mmol). It was caped and inerted with nitrogen. A degassed mixture of 1-bromo-3-(trifluoromethyl)benzene (50 µL, 0.36 mmol) and 3-methoxyaniline (50 µL, 0.45 mmol) in anisole (2 mL) wad added at rt. The catalyst solution was added to the reaction mixture. The nitrogen inlet was removed and the vial was inserted into an alumina block at 100°C. The reaction was stirred over night. After 19h, the reaction was cooled down and filtered through celite. The filtrate was concentrated. Large amounts of anisole was present. No product was detected by LCMS. The sample was descarded.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC(=CC(=C1)Br)C(F)(F)F;amine:CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2, Reagents are:Solvent:C1COCCO1;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;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];Base:CC(C)(C)[O-].[Na+], and Products are 0:CC(C)(C)OC(=O)N1CC2CC1CN2C3=CC=CC(=C3)C(F)(F)F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A 50 ml round bottom equipped with stir bar was charged with binap (0.219 g, 0.34 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.132 g, 0.14 mmol) dissolved in dioxane (6 mL). This was degassed and purged with nitrogen and stirred at RT for 10 mins. 1-bromo-3-(trifluoromethyl)benzene (0.301 mL, 2.16 mmol) followed by tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.3 g, 1.44 mmol) and SODIUM TERT-BUTOXIDE (0.570 g, 5.75 mmol) were added, and the reaction was stirred at 180 °C for 5 min (see notes). The solution was filtered trough celite, diluted with EtOAc and washed with saturated NaHCO3 solution. The aqueous phase was extracted with EtOAc (3X20mL), combined, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude material was loaded on a Snap KP-SIL 25g column and purified on a Biotage SP4 instrument, eluting with 10% to 35% ethyl acetate in heptane to provide tert-butyl 5-(3-(trifluoromethyl)phenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.489 g, 99 %) as an oil.

Here is a chemical reaction formula: Reactants are:amine:CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1CN2;aryl halide:C1=CC(=CC(=C1)Br)C(F)(F)F, Reagents 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;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];Solvent:C1COCCO1;Base:CC(C)(C)[O-].[Na+], and Products are 0:CC(C)(C)OC(=O)N1CC2CC1CN2C3=CC=CC(=C3)C(F)(F)F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A 50 ml round bottom equipped with stir bar was charged with binap (0.146 g, 0.23 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.088 g, 0.10 mmol) dissolved in dioxane (5 mL). This was degassed and purged with nitrogen and stirred at RT for 10 mins. 1-bromo-3-(trifluoromethyl)benzene (0.323 g, 1.44 mmol) followed by tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.2 g, 0.96 mmol) and SODIUM TERT-BUTOXIDE (0.380 g, 3.83 mmol) were added, and the reaction was stirred at 80 °C for 2 hrs. The solution was diluted with EtOAc and washed with saturated NaHCO3 solution. The aqueous phase was extracted with EtOAc (3X20mL), combined, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude material was loaded on a Snap KP-SIL 25g column and purified on a Biotage SP4 instrument, eluting with 10% to 35% ethyl acetate in heptane to provide tert-butyl 5-(3-(trifluoromethyl)phenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.305 g, 93 %) as an oil.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CN=C(C=C1Cl)Cl;amine:CC1=NC(=NC=C1)N, Reagents are:Solvent:C1COCCO1;Base:C(=O)([O-])[O-].[Cs+].[Cs+];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;metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:CC1=NC(=NC=C1)NC2=NC=CC(=C2)Cl, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Palladium(II) acetate (0.607 g, 2.70 mmol) was added to 2,4-dichloropyridine (5.00 g, 33.79 mmol), 4-methylpyrimidin-2-amine (3.69 g, 33.79 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (2.346 g, 4.05 mmol) and Cesium carbonate (22.02 g, 67.57 mmol) in dioxane (150 mL) at 20ºC under nitrogen. The resulting suspension was stirred at 100 °C for 90 minutes. Complete reaction by LCMS, cooled to room temperature. The reaction mixture was then filtered, washed with DCM and filtrate concentrated _in vacuo_ to give a yellow gum. This was then dissolved in DCM (200 mL), washed with water (200 mL) and brine (200 mL). The organic layer was passed through phase separating cartridge and concentrated under reduced pressure. The crude product was suspended in DCM, isolubles filtered off and dried to give EN01580-50-1, N-(4-chloropyridin-2-yl)-4-methylpyrimidin-2-amine (2.859 g, 38.3 %), as a yellow solid. The fltrate was then purified by flash silica chromatography, elution gradient 0 to 5% MeOH in DCM. No separation acheived so all fractions containing product concentrated _in vacuo_. The residue was suspended in acetonitile/water, insolubles filtered off and dried to give EN01580-50-2, N-(4-chloropyridin-2-yl)-4-methylpyrimidin-2-amine (0.934 g, 12.5 %), as a yellow solid. The filtrate was then 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 0.1% formic acid) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford EN01580-50-3, N-(4-chloropyridin-2-yl)-4-methylpyrimidin-2-amine (0.511 g, 6.85 %), as a white solid.

Here is a chemical reaction formula: Reactants are:amine:C[C@@H]1CN(CCN1)C(=O)OC(C)(C)C;aryl halide:C1=CC(=CC=C1O)Br, Reagents are:Solvent:C1CCOC1;metal and ligand:CC(C)(C)P(C(C)(C)C)C(C)(C)C;metal and ligand:CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd];Base:CC(C)(C)[O-].[K+], and Products are 0:C[C@@H]1CN(CCN1C2=CC=C(C=C2)O)C(=O)OC(C)(C)C, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A mixture of (R)-tert-butyl 3-methylpiperazine-1-carboxylate (0.025 g, 0.12 mmol), 4-bromophenol (0.043 g, 0.25 mmol), bis(tri-t- butylphosphine)palladium(0) (6.38 mg, 0.01 mmol) and [Reactants] in THF (2 mL) was flushed with nitrogen and sealed into a microwave tube. The reaction was heated to 100 °C for 20 minutes in the microwave reactor and cooled to RT. No trace of desired product by LCMS. The reaction was not progressed further.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC(=C(C=C1C(F)(F)F)I)F;amine:COC1=NC(=NC=C1Br)N, Reagents are:Solvent:CC1=CC=CC=C1;metal and ligand:C1=COC(=C1)P(C2=CC=CO2)C3=CC=CO3;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:COC1=NC(=NC=C1Br)NC2=C(C=CC(=C2)C(F)(F)F)F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: To a microwave vial was added a mixture of 5-bromo-4-methoxypyrimidin-2-amine (0.513 g, 2.51 mmol), diacetoxypalladium (0.055 g, 0.245 mmol), tri(furan-2-yl)phosphine (0.126 g, 0.54 mmol), 1-fluoro-2-iodo-4-(trifluoromethyl)benzene (0.98 g, 3.38 mmol) and toluene (17 mL) under inert atmosphere. The reaction mixture was sealed and heated at 90 °C under 15h. The LCMS indicated no reaction ??? The sample discarded.

Here is a chemical reaction formula: Reactants are:aryl halide:COC1=C(C=CC(=C1)Cl)I;amine:CN1CCNCC1, Reagents are:Base:CC(C)(C)[O-].[Na+];Solvent:CC1=CC=CC=C1;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;metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:CN1CCN(CC1)C2=C(C=C(C=C2)Cl)OC, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Palladium II acetate (25.09 mg, 0.11 mmol) was added to 4-chloro-1-iodo-2-methoxybenzene (300 mg, 1.12 mmol), 1-methylpiperazine (0.124 ml, 1.12 mmol), sodium 2-methylpropan-2-olate (215 mg, 2.23 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (323 mg, 0.56 mmol) in toluene (4 ml) at room temperture under nitrogen. The resulting mixture was stirred at 100oC overnight. The reaction mixture was filtered through celite and then concentrated under reduced pressure. The crude product was then taken up in DCM and washed with water. The crude product was purified by chromatography in DCM:MeOH 0-->10% to afford 1-(4-chloro-2-methoxyphenyl)-4-methylpiperazine (171 mg, 63.6 %) as yellow oil. This was carried through to the next reaction immediately as it is a controlled substance.

Here is a chemical reaction formula: Reactants are:amine:C1=CC=C2C(=C1)C=C(C=N2)N;aryl halide:C1CN(CC2=C1C(=NC=C2)Cl)S(=O)(=O)C3=CC=CO3, Reagents 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;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];Solvent:CC(C)(C)O;Base:CC(C)(C)[O-].[Na+], and Products are 0:C1CN(CC2=C1C(=NC=C2)NC3=CC4=CC=CC=C4N=C3)S(=O)(=O)C5=CC=CO5, please give me the reaction condition of this formula.

The condition of this chemical reaction is: The yellow residue containing 5-chloro-2-(furan-2-ylsulfonyl)-1,2,3,4-tetrahydro-2,6-naphthyridine (0.057 g, 0.19 mmol) and quinolin-3-amine (0.096 g, 0.67 mmol) from 02910-38 was dissolved in toluene (1 mL) and tert-butanol (0.170 mL). The resulting yellow solution was degassed (vacuum) and then tris(dibenzylideneacetone)dipalladium(0) (4.19 mg, 4.58 µmol), Xantphos (5.52 mg, 9.54 µmol), and sodium tert-butoxide (0.026 g, 0.27 mmol) were added. Another 2 mL of toluene and 0.340 mL of tert-butanol were also added. The resulting mixture was subjected to microwave conditions for 30 min (300W, 110°C) and then cooled. The biphasic red-brown/brown-black mixture was poured into saturated aqueous sodium chloride and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by falsh column chromatography (SiO2, 0-100% ethyl acetate in hexanes) and then preparative LCMS (C18, ethanol in water containing ammonium carbonate, pH 10). The resulting white solid was repurified a third time via preparative HPLC (C18, acetonitrile in water containing ammonium carbonate, pH 10) to afford 6-(furan-2-ylsulfonyl)-N-(quinolin-3-yl)-5,6,7,8-tetrahydro-2,6-naphthyridin-1-amine (7.60 mg, 9.80 %) of 95% purity as a white solid.

Here is a chemical reaction formula: Reactants are:amine:C1=CC=NC(=C1)N;aryl halide:C1=CC(=CN=C1)Br, Reagents are:Solvent:COCCOC;Base:CC(C)(C)[O-].[Na+];metal and ligand:CC(C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CCCC1.[Fe];metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:C1=CC=NC(=C1)NC2=CN=CC=C2, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Stock solution: 0.01 mmol Pd and ligand were dissolved in 2 mL DME. 3-bromopyridine (0.482 mL, 5.00 mmol) was dissolved in DME (10 mL). To the solution was added the stock solution, and sodium tert-butoxide (0.673 g, 7.00 mmol). To the mixture was added a solution of pyridin-2-amine (0.565 g, 6.00 mmol) in DME (10 mL). The mixture was heated at 90 °C overnight. The mixture was filtered. The filtrate was concentrated, and the compound was purified by preparative HPLC on a XBridge C18 column (10 µm 250x50 ID mm) using a gradient of 0-50% acetonitrile in H2O/ACN/NH3 95/5/0.2 buffer over 15 minutes with a flow of 100 mL/min. The compounds were detected by UV at 254nm. To the fractions (ca. 60mL) were added 5 mL of HOAc. The product was freezing-dried to give the product N-(pyridin-3-yl)pyridin-2-amine (0.190 g, 22.20 %).

Here is a chemical reaction formula: Reactants are:amine:CC(=O)N(C)C1=CC2=C(C=C1)C=CN2;aryl halide:C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl, Reagents are:Solvent:CC(=O)N(C)C;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;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];Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:CC(=O)N(C)C1=CC2=C(C=C1)C=CN2C3=NC4=C(C=NN4C(=C3)NC5CC5)C#N, please give me the reaction condition of this formula.

The condition of this chemical reaction is: In microwave tube, added 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (84mg), N-(1H-indol-6-yl)-N-methylacetamide (67 mg), Pd2(dba)3 (16 mg), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (20mg) cesium carbonate(129 mg) in anhydrous DMA (0.5mL). under microwave 150C for 30 min. the mixture was filtered. washed with MeOH. combinde organic solvent, dried to dryness. The residue solid was washed with MeOH to give about 22mg offwhite solid (product.

Here is a chemical reaction formula: Reactants are:aryl halide:CS(=O)(=O)CC1=C(C=CC(=C1)N)Cl;amine:C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl, Reagents are:Solvent:CC(=O)N(C)C;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;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];Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:CS(=O)(=O)CC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)Cl, please give me the reaction condition of this formula.

The condition of this chemical reaction is: In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (88 mg, 0.38 mmol), [Reactants], and cesium carbonate (135 mg, 0.41 mmol) in DMA (0.5 mL) ([VOLUME]),Pd2(dba)3 (17.24 mg, 0.02 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (21.79 mg, 0.04 mmol) were added. to give a brown suspension. The vial was filled with N2, 150C microwave for 30 min. LCMS showed completion. added DMF(3 mL), filtered through celite. concentrated. The residue was washed with EtOAc and water, MeoH to give about 55mg light brown solid

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC(=C(C=C1F)C=O)Br;amine:C1CCNC1, Reagents 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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:C(=O)([O-])[O-].[Cs+].[Cs+];Solvent:CC1=CC=CC=C1, and Products are 0:C1CCN(C1)C2=C(C=C(C=C2)F)C=O, please give me the reaction condition of this formula.

The condition of this chemical reaction is: To a mixture of pyrrolidine (328 mg, 3.05 mmol), 2-bromo-4-fluorobenzaldehyde (619 mg, 3.05 mmol) in toluene (10 ml) was added Cs2CO3 (2.48g, 7.62 mmol), BINAP (95 mg ) and palladium(II) acetate (35 mg) was added. The mixture was purged with Ar for 5 min, then heated at 95 oC for 4 hrs. After cooled to RT, EtOAc (30 mL) was added. The organic layer was washed with water (3 x 30 mL), brine (30 mL), dried over MgSO4, filetred and concentrated. The residue was purified via combiflush (0 - 20% EtOAc/Hexane; 40 g column) to give the desired product as a clear reddish liquid. LCMS and H-NMR look good. 290 mg Conclusion: reaction progressed to give desired product in 49% yield.

Here is a chemical reaction formula: Reactants are:amine:C1COCC(=O)N1;aryl halide:C1=CC(=NC(=C1)Br)Br, Reagents 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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:C(=O)([O-])[O-].[Cs+].[Cs+];Solvent:C1COCCO1, and Products are 0:C1COCC(=O)N1C2=NC(=CC=C2)Br, please give me the reaction condition of this formula.

The condition of this chemical reaction is: **_September 10 2015_** morpholin-3-one (1g, 9.89 mmol), 2,6-dibromopyridine (3.51 g, 14.84 mmol), PdOAc2 (0.222 g, 0.99 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.145 g, 1.98 mmol) and CS2CO3 (6.12 g, 18.79 mmol) in 1,4-dioxane (20 mL) were heated at 80 °C for 12 hours. **_September 11 2015_** LCMS showed no precursor and 37% of the desired mass MH+ 257/259 @ 0.86 min along with lots of unknowns on a 2-min basic run. The reaction was cooled to RT, and filtered off the solid (Cs2CO3). The filter was concentrated, re-dissolved in EtOAc, washed with waster, dried through MgSO4, and evaporated to give an orange gum. **_September 14 2015_** The orange gum was added to a Biotage column and was eluted with 10-100%EtOAc in Heptane. Collected fractions. The column was stuck as 37% EtOAc in Heptane. A lot of CH2Cl2 was pushed through the column manually, and then continued the elution with 0-100% EtOAc in DCM. Collected fractions. The product fractions were identified, combined based on LCMS and TLC, and evaporated to give a white solid as the desired product (EN07946-27-001). Based on LCMS, it was 98% pure; based on NMR in DMSO, it was > 95%pure; _however, based on NMR in CDCl3, there were ~30% impurity in the aromatic proton region._ The product was used for next step without further purification.

Here is a chemical reaction formula: Reactants are:aryl halide:C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl;amine:CC(=O)NC1=CC=CC(=C1)N, Reagents are:Base:C(=O)([O-])[O-].[Cs+].[Cs+];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;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];Solvent:CC(=O)N(C)C, and Products are 0:CC(=O)NC1=CC=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N, please give me the reaction condition of this formula.

The condition of this chemical reaction is: in microwave tube was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (80 mg, 0.34 mmol), N-(3-aminophenyl)acetamide (51.4 mg, 0.34 mmol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (19.81 mg, 0.03 mmol) in DMA (0.5 mL).Pd2(dba)3 (15.68 mg, 0.02 mmol) and cesium carbonate (123 mg, 0.38 mmol) were added. degassed, filled with N2.capped. then microwave 150C for 30 min. added 2 mL of MeOH, filtered through celite. concentrated. The residue was purified by ISCO (Hex to Hex:EtOAc=1:4 to 1:1 to EtOAc), collected prod fractions. concentrated to brown semi-solid

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC=C(C=C1)Br;amine:C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCNCC4, Reagents 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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:C(=O)([O-])[O-].[Cs+].[Cs+];Solvent:CC1=CC=CC=C1, and Products are 0:C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCN(CC4)C5=CC=CC=C5, please give me the reaction condition of this formula.

The condition of this chemical reaction is: cesium carbonate (123 mg, 0.38 mmol) was added to a solution of (4-cyclobutylpiperazin-1-yl)(7-azaspiro[3.5]nonan-2-yl)methanone (100 mg, 0.34 mmol), PdOAc2 (7.70 mg, 0.03 mmol), BINAP (42.7 mg, 0.07 mmol) and bromobenzene (56.6 mg, 0.36 mmol) in toluene (5 mL). The reaction mixture was heated to 110°C for 18hrs. The room temperature cooled down mixture was filtered over celite. The solvent was concentrated. The product was purified by preparative HPLC using a low pH shallow gradient method (Mobile phase: 20-40% B; A: H2O with 0.05% TFA , B: CH3CN, 25 min. run) on Luna 15 m, C8 (2), 21.2x250 mm Phenomenex reverse phase column to provide (4-cyclobutylpiperazin-1-yl)(7-phenyl-7-azaspiro[3.5]nonan-2-yl)methanone (59.0 mg, 46.8 %) as white solid. 1H NMR (400 MHz, CHLOROFORM- _d_ ) d ppm 1.60 - 1.75 (m, 4 H) 1.75 - 1.81 (m, 2 H) 1.81 - 1.95 (m, 2 H) 1.96 - 2.10 (m, 4 H) 2.10 - 2.20 (m, 2 H) 2.21 - 2.35 (m, 4 H) 2.71 (dq, _J_ =8.01, 7.75 Hz, 1 H) 3.00 - 3.11 (m, 2 H) 3.11 - 3.26 (m, 3 H) 3.31 - 3.42 (m, 2 H) 3.56 - 3.70 (m, 2 H) 6.82 (t, _J_ =7.23 Hz, 1 H) 6.93 (d, _J_ =7.81 Hz, 2 H) 7.18 - 7.29 (m, 2 H) HRMS _m/z_ calcd for C23H33N3O 368.26964 [M+H]+, found 368.26981. MS _m/z_ 368.3 [M+H]\+ (ES+)

Here is a chemical reaction formula: Reactants are:aryl halide:C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl;amine:CC(=O)NC1=C(C=CC(=C1)N)N2CC[C@@H](C2)N(C)C, Reagents 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;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];Solvent:CC(=O)N(C)C;Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N5CC[C@@H](C5)N(C)C, please give me the reaction condition of this formula.

The condition of this chemical reaction is: in microwave tube was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (100mg, 0.43 mmol), [Reactants], and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (24.76 mg, 0.04 mmol) in DMA (1.0 mL).Pd2(dba)3 (19.60 mg, 0.02 mmol) and cesium carbonate (279 mg, 0.86 mmol) were added. degassed, filled with N2.capped. then microwave 150C for 30 min. filtered, then concentrated. The crude material was purified by ISC(Hex to Hex:EtOAc=1;1 to EtOAc to EtOAc:MeOH=10:1 to EtOAc:MeOH:Et3N=10:1:0.1)) to give no very pure product. collect the product fraction, concentrated to dryness. no pure enough, tried to form solid. it failed sent to ananlytic group for purification. came back. it was OK 1TFA salt. NMR LCMS are OK

Here is a chemical reaction formula: Reactants are:aryl halide:CC1=CC(=CC(=N1)Cl)CO;amine:CC(C)(C)OC(=O)N, Reagents are:Solvent:C1COCCO1;Base:C(=O)([O-])[O-].[Cs+].[Cs+];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;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], and Products are 0:CC1=CC(=CC(=N1)NC(=O)OC(C)(C)C)CO, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A 2.0-5.0 mL microwave vial was charged with XANTPHOS (14.66 mg, 0.03 mmol), Pd2(dba)3 (29.1 mg, 0.03 mmol), CESIUM CARBONATE (155 mg, 0.48 mmol),(2-chloro-6-methylpyridin-4-yl)methanol (50 mg, 0.32 mmol), tert-butyl carbamate (44.6 mg, 0.38 mmol) and dioxane (3 mL). The reaction mixture was degassed for 2 minutes with nitrogen, and then the reaction mixture was stirred at 80°C under microwave irradiation for 30 min. Water (5 mL) was added and the mixture was washed using EtOAc (3 x 10 mL). The organic layers were combined, dried using MgSO4, filtered and concentrated. The crude material was loaded on a 12g silica gel column and purified on a Teledyne Isco instrument, eluting with 0% to 20% EtOAc in DCM. The product that seems to be the compound was collected. Unfrtunately NMR showed that this compound is dba. The compound was not isolated.

Here is a chemical reaction formula: Reactants are:amine:CC(C)C1=C(C=C(C=C1)N)NC(=O)C;aryl halide:C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl, Reagents 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;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];Base:C(=O)([O-])[O-].[Cs+].[Cs+];Solvent:CC(=O)N(C)C, and Products are 0:CC(C)C1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)NC(=O)C, please give me the reaction condition of this formula.

The condition of this chemical reaction is: In a 5 mL microwave reactor vial was charged with 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.070 g, 0.30 mmol), N-(5-amino-2-isopropylphenyl)acetamide (0.058 g, 0.30 mmol), Pd2(dba)3 (0.014 g, 0.01 mmol), Pd2(dba)3 (0.014 g, 0.01 mmol) and cesium carbonate (0.293 g, 0.90 mmol), the vessel was sealed with a microwave cap, and degassed and refilled with argon for 3 times. DMA (0.5 mL)was added via syringe. The resulting suspension heated at 140°C for 30mins in microwave. LCMS analysis showed product mass and byproduct. The reaction mixture was concentrated. 10% MeOH in DCM was added to the resulting residue to generate a brown suspension. This brown suspension was filtered to remove inorganic impurity. The filtrate was concentrated to give a brown crude product. This material was loaded on isco column (12g, DCM to 10% MeCNin DCM to 25% MeCN in DCM to 50%MeCN to 100% MeCM) and purified. Only 3mg of product was isolated. The ISCO column was saved. Some solid was presented on the top of the column. This solid was recovered, washed with water and dried under high vacuum at 60C to give N-(5-(3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-ylamino)-2-isopropylphenyl)acetamide (0.012 g, 10.29 %) as an offwhite solid.

Here is a chemical reaction formula: Reactants are:amine:CC1=CSC(=N1)N;aryl halide:C1CN(C(=O)OC1)C2=NC(=CC=C2)Br, Reagents 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;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.[Pd];Solvent:CC1=CC=CC=C1;Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:CC1=CSC(=N1)NC2=NC(=CC=C2)N3CCCOC3=O, please give me the reaction condition of this formula.

The condition of this chemical reaction is: **_September 21 2015_** 4-methylthiazol-2-amine (85 mg, 0.74 mmol), 3-(6-bromopyridin-2-yl)-1,3-oxazinan-2-one (191 mg, 0.74 mmol), 3-(6-bromopyridin-2-yl)-1,3-oxazinan-2-one (191 mg, 0.74 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (43.1 mg, 0.07 mmol) and cesium carbonate (291 mg, 0.89 mmol) in toluene (5 mL) were microwaved at 120 °C under N2 for one hour. LCMS showed no precursors and 51% of the desired mass MH+291 @ 0.86 min on a 2-min basic run. The reaction mixture was diluted with EtOAc, washed with water, filtered, and evaporated to give a brown solid as the crude product. The crude product was added to a Biotage column, and was eluted with 15-100%EtOAc in Heptane. Collected fractions. **_September 22 2015_** Based on TLC and LCMS, the product fractions were combined, and evpoarated to give an yellow-brown solid (94 mg). Based on LCMS, it was only 89% pure. Based on LCMS, it was 96% pure; based on NMR, it was > 95% pure.

Here is a chemical reaction formula: Reactants are:amine:CC1=CSC(=N1)N;aryl halide:C1CN(C(=O)OC1)C2=NC(=CC=C2)Br, Reagents are:Solvent:CC1=CC=CC=C1;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;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.[Pd];Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:CC1=CSC(=N1)NC2=NC(=CC=C2)N3CCCOC3=O, please give me the reaction condition of this formula.

The condition of this chemical reaction is: **_September 28 2015_** 4-methylthiazol-2-amine (300 mg, 2.63 mmol), 3-(6-bromopyridin-2-yl)-1,3-oxazinan-2-one (676 mg, 2.63 mmol), 3-(6-bromopyridin-2-yl)-1,3-oxazinan-2-one (676 mg, 2.63 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (152 mg, 0.26 mmol) and cesium carbonate (1027 mg, 3.15 mmol) in toluene (13 mL)/DMF (2.00 mL) were microwaved at 115 °C under N2 for one hour. (Note: Based on the observation in EN07946-41, _DMF was added to improve the heating due to the low thremal absorbance of toluene.)_ One hour later, LCMS showed 13% of the precursor MH+257/259 @ 0.84 min and 36% of the desired mass MH+291 @ 0.86 min along with some unknowns on a 2-min basic run. The reaction seemed not complete. The reaction was microwaved at 115 °C for another 45 min. One hour and 45 min later, LCMS showed 7% of the precursor MH+257/259 @ 0.84 min and 37% of the desired mass MH+291 @ 0.86 min along with some unknowns on a 2-min basic run. The reaction seemed stuck, and was cooled to RT. **_September 29 2015_** The reaction mixture was diluted with EtOAc, washed with water, filtered, and evaporated to give a brown solid as the crude product. The crude product was added to a Biotage column, and was eluted with 15-100%EtOAc in Heptane. Collected fractions. **_September 30 2015_** Based on TLC and LCMS, the product fractions were combined, and evpoarated to give an yellow-brown solid, which was vacuumed overnight at 40 °C **_OCtober 1 2015_** Based on LCMS, it was 100% pure; based on NMR, it was 90~95% pure, and contained 0.1eq of DMF.

Here is a chemical reaction formula: Reactants are:aryl halide:CC1=CC(=C(C=C1)NC2=C(N=NC3=C2C=CC(=C3)Br)C#N)F;amine:C1CNCCN1, Reagents are:Base:CC(C)(C)[O-].[Na+];Solvent:CC(=O)N(C)C;metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C;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], and Products are 0:CC1=CC(=C(C=C1)NC2=C(N=NC3=C2C=CC(=C3)N4CCNCC4)C#N)F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A 1L flask was charged with 7-bromo-4-(2-fluoro-4-methylphenylamino)cinnoline-3-carbonitrile (3.93 g, 11.00 mmol), Piperazine (3.88 ml, 49.51 mmol), Tris(dibenzylideneacetone)dipalladium (0) (0.806 g, 0.88 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.787 g, 1.65 mmol) and Sodium tert-butoxide (3.37 ml, 27.51 mmol). The atmosphere was evacuated and replaced with N2(g) and DMA (157 ml) was added to the mixture. The reaction mixture was stirred at 100 °C for 1h. The reaction mixture was cooled to rt, adsorbed on silica gel and flash chromatography using DCM to DCM/MeOH/NH4OH (10:1:0.1) provided the desired adduct as a light brown solid.

Here is a chemical reaction formula: Reactants are:aryl halide:CC1=CC(=C(C=C1)NC2=C(N=NC3=C2C=CC(=C3)Br)C#N)F;amine:C1CNCCN1, Reagents are:metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C;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];Solvent:CC(=O)N(C)C;Base:CC(C)(C)[O-].[Na+], and Products are 0:CC1=CC(=C(C=C1)NC2=C(N=NC3=C2C=CC(=C3)N4CCNCC4)C#N)F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A 100 mL flask was charged with 7-bromo-4-(2-fluoro-4-methylphenylamino)cinnoline-3-carbonitrile (0.64 g, 1.79 mmol), Piperazine (0.631 ml, 8.06 mmol), Tris(dibenzylideneacetone)dipalladium (0) (0.131 g, 0.14 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso- propyl-1,1'-biphenyl (0.128 g, 0.27 mmol) and Sodium tert-butoxide (0.548 ml, 4.48 mmol). The mixture was suspended in DMA (25.6 ml) and the reaction mixture was stirred at 100 °C for 30min. The reaction mixture was cooled to rt, diluted with DCM/MeOH (10:1) and filtered over a pad of celite. The filterate was concentrated under reduced pressure, adsorbed onto silica gel and flash chromatography using DCM to DCM/MeOH/NH4OH (10:1:0.1) provided the desired compound as a light orange solid.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CN=C(C=C1Cl)Cl;amine:CC1=CC(=NC(=N1)C)N, Reagents are:Solvent:C1COCCO1;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;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:CC1=CC(=NC(=N1)C)NC2=NC=CC(=C2)Cl, please give me the reaction condition of this formula.

The condition of this chemical reaction is: Palladium(II) acetate (0.607 g, 2.70 mmol) was added to 2,4-dichloropyridine (5.00 g, 33.79 mmol), 2,6-dimethylpyrimidin-4-amine (4.16 g, 33.79 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (2.346 g, 4.05 mmol) and Cesium carbonate (22.02 g, 67.57 mmol) in dioxane (150 mL) at 20ºC under nitrogen. The resulting suspension was stirred at 100 °C for 90 minutes. Complete reaction by LCMS, cooled to room temperature. The reaction mixture was then filtered, washed with DCM and filtrate concentrated _in vacuo_ to give a yellow gum. This was then dissolved in DCM (200 mL), washed with water (200 mL) and brine (200 mL). The organic layer was passed through phase separating cartridge and concentrated under reduced pressure. The crude product was purified by flash silica chromatography, elution gradient 0 to 5% MeOH in DCM. Pure fractions were evaporated to dryness to afford N-(4-chloropyridin-2-yl)-2,6-dimethylpyrimidin-4-amine (4.86 g, 61.2 %) as a yellow solid.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC(=C(C=C1F)Cl)Br;amine:C1CNCCC1=O, Reagents are:Base:CC(C)(C)[O-].[Na+];metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C;metal and ligand:CC(=O)O.CC(=O)O.[Pd];Solvent:CC1=CC=CC=C1, and Products are 0:C1CN(CCC1=O)C2=C(C=C(C=C2)F)Cl, please give me the reaction condition of this formula.

The condition of this chemical reaction is: To a round bottom flask was added palladium(II) acetate (0.012 g, 0.06 mmol), dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.026 g, 0.06 mmol), and sodium tert-butoxide (0.213 g, 2.21 mmol). Added 5 mL toluene/t-butanol mix and purged with nitrogen. Added piperidin-4-one (0.15 g, 1.11 mmol), in 3 mL tol/tbuoh (slurry), followed by 1-bromo-2-chloro-4-fluorobenzene (0.255 g, 1.22 mmol), in 2 mL tol/tbuoh. Flushed with additional nitrogen and then heated to 120oC overnight. Let reaction mixture cool to room temperature and filtered through Celite. Rinsed repeatedly with EtOAc and concentrated in vacuo. Purified via ISCO 12g SiO2 column using 0-20% hexanes/ethyl acetate. Fractions 19 and 20 were combined and concentrated to afford a white solid. NMR (I200805922.42) shows a mess. Discarded. Will try another way.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC=NC(=C1)Br;amine:C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCNCC4, Reagents are:Base:C(=O)([O-])[O-].[Cs+].[Cs+];Solvent:CC1=CC=CC=C1;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;metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:C1CC(C1)N2CCN(CC2)C(=O)C3CC4(C3)CCN(CC4)C5=CC=CC=N5, please give me the reaction condition of this formula.

The condition of this chemical reaction is: cesium carbonate (123 mg, 0.38 mmol) was added to a solution of (4-cyclobutylpiperazin-1-yl)(7-azaspiro[3.5]nonan-2-yl)methanone (100 mg, 0.34 mmol), PdOAc2 (7.70 mg, 0.03 mmol), BINAP (42.7 mg, 0.07 mmol) and 2-bromopyridine (56.9 mg, 0.36 mmol) in toluene (2 mL). The reaction mixture was heated to 110°C for 18hrs. The room temperature cooled down mixture was filtered over celite. The solvent was concentrated. The product was purified by preparative HPLC using a low pH shallow gradient method (Mobile phase: 20-40% B; A: H2O with 0.05% TFA , B: CH3CN, 25 min. run) on Luna 15 m, C8 (2), 21.2x250 mm Phenomenex reverse phase column to provide (4-cyclobutylpiperazin-1-yl)(7-(pyridin-2-yl)-7-azaspiro[3.5]nonan-2-yl)methanone (54.1 mg, 42.8 %) as white solid. 1H NMR (400 MHz, CHLOROFORM- _d_ ) d ppm 1.62 - 1.75 (m, 4 H) 1.75 - 1.81 (m, 2 H) 1.81 - 1.94 (m, 2 H) 1.98 - 2.10 (m, 4 H) 2.12 - 2.21 (m, 2 H) 2.23 - 2.32 (m, 4 H) 2.71 (quin, _J_ =7.91 Hz, 1 H) 3.05 - 3.14 (m, 2 H) 3.14 - 3.26 (m, 3 H) 3.33 - 3.40 (m, 2 H) 3.58 - 3.68 (m, 2 H) 7.09 - 7.15 (m, 1 H) 7.16 - 7.21 (m, 1 H) 8.06 (dd, _J_ =4.49, 1.37 Hz, 1 H) 8.31 (d, _J_ =2.73 Hz, 1 H) HRMS _m/z_ calcd for C22H32N4O 369.26489 [M+H]+, found 369.26461 . MS _m/z_ 369.2 [M+H]\+ (ES+)

Here is a chemical reaction formula: Reactants are:amine:CC(=O)NC1=C(C=CC(=C1)N)N(C)CCN(C)C;aryl halide:C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl, Reagents 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;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];Solvent:CC(=O)N(C)C;Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N(C)CCN(C)C, please give me the reaction condition of this formula.

The condition of this chemical reaction is: In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (200 mg, 0.86 mmol), N-(5-amino-2-((2-(dimethylamino)ethyl)(methyl)amino)phenyl)acetamide (214 mg, 0.86 mmol), and cesium carbonate (363 mg, 1.11 mmol) in DMA (0.5 mL) ([VOLUME]),Pd2(dba)3 (39.2 mg, 0.04 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (49.5 mg, 0.09 mmol) were added. to give a brown suspension. The vial was filled with N2, 150C microwave for 30 min. LCMS showed completion. concentrated. loaded on ISCO (Hex to Hex:EtOAc To EtOAc:MeOH=10:1 to EtOAc:MeOH:Et3N=10:1:0.1) to give yellow sticky oil. tried to use EtOAc(1 mL) as solvent to make the product to form crys. finally the solid was formed and washed with EtOA (1mL) and Et2O(2mL) to give 86mg white solid NMR LCMS are OK

Here is a chemical reaction formula: Reactants are:aryl halide:C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl;amine:CC(=O)NC1=C(C=CC(=C1)N)N(C)CCN(C)C, Reagents are:Solvent:CC(=O)N(C)C;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;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];Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:CC(=O)NC1=C(C=CC(=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)N(C)CCN(C)C, please give me the reaction condition of this formula.

The condition of this chemical reaction is: In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (80 mg, 0.34 mmol), [Reactants], and cesium carbonate (145 mg, 0.45 mmol) in DMA (0.5 mL) ([VOLUME]),Pd2(dba)3 (15.68 mg, 0.02 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (19.81 mg, 0.03 mmol) were added. to give a brown suspension. The vial was filled with N2, 150C microwave for 30 min. LCMS showed completion. concentrated. loaded on ISCO (Hex to Hex:EtOAc To EtOAc:MeOH=10:1 to EtOAc:MeOH:Et3N=10:1:0.1) to give yellow solid. This yellow solid was washed with EtOAc(1mL) and Et2O(2mL) to give 50 mg pure compound. NMR, 1H,HPLC are OK, see attachment

Here is a chemical reaction formula: Reactants are:aryl halide:C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl;amine:CC1=C(C=C(C=C1)N)NC(=O)C, Reagents 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;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];Solvent:CC(=O)N(C)C;Base:C(=O)([O-])[O-].[Cs+].[Cs+], and Products are 0:CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)NC(=O)C, please give me the reaction condition of this formula.

The condition of this chemical reaction is: in microwave tube was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (400 mg, 1.71 mmol), N-(5-amino-2-methylphenyl)acetamide (281 mg, 1.71 mmol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (99 mg, 0.17 mmol) in DMA (0.5 mL).Pd2(dba)3 (78 mg, 0.09 mmol) and cesium carbonate (1116 mg, 3.42 mmol) were added. degassed, filled with N2.capped. then microwave 150C for 30 min. The reaction was divided by 4, run 100mg scale four time. combined all of crude mixture, filtered and washed with MeOH. the organic solvent was removed. The black residue was tried to purifed by ISCO. impurity and prod came out together too quickly. purified by glass-clumn (150g silica, Hex to EtOAc:Hex =1:1 to EtOAc), colleceted product fraction. concentrated to give offwhite solid. LCMS showed about 10% impurity. The solid was washed with hot EtOAc(5 mL), filtered. The solild was washed with water (1mL) and EtOAc(1 mL) to give about 110mg white solid. LCMS and NMR are OK, see attachment. low yield was due to hot EtOAc wash, lost some prod.

Here is a chemical reaction formula: Reactants are:amine:CC1=C(C=C(C=C1)N)NC(=O)C;aryl halide:C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl, Reagents are:Base:C(=O)([O-])[O-].[Cs+].[Cs+];Solvent:CC(=O)N(C)C;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;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], and Products are 0:CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)NC(=O)C, please give me the reaction condition of this formula.

The condition of this chemical reaction is: in microwave tube was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (80 mg, 0.34 mmol), N-(5-amino-2-methylphenyl)acetamide (56.2 mg, 0.34 mmol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (19.81 mg, 0.03 mmol) in DMA (0.5 mL).Pd2(dba)3 (15.68 mg, 0.02 mmol) and cesium carbonate (123 mg, 0.38 mmol) were added. degassed, filled with N2.capped. then microwave 150C for 30 min. added 2 mL of MeOH, filtered through celite. concentrated. The residue was purified by ISCO (Hex to Hex:EtOAc=1:4 to 1:1 to EtOAc), collected prod fractions. concentrated to give offwhite solid. This solid was washed with 0.5 mL of EtOAc to give pure prod

Here is a chemical reaction formula: Reactants are:amine:CC1=C(C=C(C=C1)N)NC(=O)C;aryl halide:C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl, Reagents are:Base:C(=O)([O-])[O-].[Cs+].[Cs+];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;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];Solvent:CC(=O)N(C)C, and Products are 0:CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)NC(=O)C, please give me the reaction condition of this formula.

The condition of this chemical reaction is: in microwave tube was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (500 mg, 2.14 mmol), N-(5-amino-2-methylphenyl)acetamide (351 mg, 2.14 mmol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (124 mg, 0.21 mmol) in DMA (2.5 mL).Pd2(dba)3 (98 mg, 0.11 mmol) and cesium carbonate (1394 mg, 4.28 mmol) were added. degassed, filled with N2.capped. then microwave 150C for 30 min. The reaction was divided by 5, run 100mg scale five time. combined all of crude mixture, filtered and washed with MeOH. the organic solvent was removed. The black residue was tried to purifed by ISCO.(40g cloumn, Hex to EtOAc:Hex =1:1 to EtOAc), colleceted product fraction. concentrated to give offwhite solid. LCMS showed about 10% impurity. The solid was washed with hot EtOAc(5 mL), filtered. The solild was washed with to give about 175mg white solid. LCMS and NMR are OK, see attachment. low yield was due to hot EtOAc wash, lost some prod.

Here is a chemical reaction formula: Reactants are:aryl halide:C1CC1NC2=CC(=NC3=C(C=NN23)C#N)Cl;amine:CC1=C(C=C(C=C1)N)NC(=O)C, Reagents are:Solvent:CC(=O)N(C)C;metal and ligand:C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4;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];Base:CC(C)(C)[O-].[Na+], and Products are 0:CC1=C(C=C(C=C1)NC2=NC3=C(C=NN3C(=C2)NC4CC4)C#N)NC(=O)C, please give me the reaction condition of this formula.

The condition of this chemical reaction is: In a 25 mL round-bottomed flask (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (40 mg, 0.17 mmol), Pd2(dba)3 (7.84 mg, 8.56 µmol), and [Reactants] in DMA (1.5 mL) ([VOLUME]) to give a black suspension.[Reactants] and N-(5-amino-2-methylphenyl)acetamide (28.1 mg, 0.17 mmol) were added. stirred at 110C for 2 days. TLC showed major is SM, small amount of product was formed/ did not workup LCMS showed 349 mass ??

Here is a chemical reaction formula: Reactants are:amine:C[C@@H]1CNCCN1C(=O)OC(C)(C)C;aryl halide:CS(=O)(=O)C1=CC=C(C=C1)Br, Reagents are:Base:CC(C)(C)[O-].[K+];Solvent:C1COCCO1;metal and ligand:CC(C)(C)P(C(C)(C)C)C(C)(C)C;metal and ligand:CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Pd], and Products are 0:C[C@@H]1CN(CCN1C(=O)OC(C)(C)C)C2=CC=C(C=C2)S(=O)(=O)C, please give me the reaction condition of this formula.

The condition of this chemical reaction is: 13-May-09 10:32:28 +0100 1-bromo-4-(methylsulfonyl)benzene (515 mg, 2.13 mmol), (R)-tert-butyl 2-methylpiperazine-1-carboxylate (426 mg, 2.13 mmol) and BIS(TRI-T- BUTYLPHOSPHINE)PALLADIUM(0) (54.3 mg, 0.11 mmol) and potassium 2-methylpropan-2-olate (352 mg, 2.98 mmol) were suspended in dioxane (10 mL) and heated to 90°C for 3 hours. LC-MS shows starting material. Reaction abandoned.

Here is a chemical reaction formula: Reactants are:aryl halide:C1=CC(=C(C=C1Br)Cl)C#N;amine:CC(C)(C)OC(=O)N1CCNCC1, Reagents are:Solvent:CC1=CC=CC=C1;Base:C(=O)([O-])[O-].[Cs+].[Cs+];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;metal and ligand:CC(=O)O.CC(=O)O.[Pd], and Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=CC(=C(C=C2)C#N)Cl, please give me the reaction condition of this formula.

The condition of this chemical reaction is: In a 250 mL round-bottomed dried flask , diacetoxypalladium (0.036 g, 0.16 mmol) was treated with 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.195 g, 0.31 mmol) under nitrogen in toluene (35 mL). The reaction was heated to 80 °C and was stirred for 10 min. To the flask was then added tert-butyl piperazine-1-carboxylate (0.602 g, 3.23 mmol), cesium carbonate (0.527 g, 1.62 mmol), potassium carbonate (0.447 g, 3.23 mmol) and 1,4,7,10,13,16-hexaoxacyclooctadecane (0.085 g, 0.32 mmol). The reaction was then treated with 4-bromo-2-chlorobenzonitrile (0.7 g, 3.23 mmol) and was allowed to stir at 80°C for 5 h. The mixture was then filtered over celite and celite was washed with heptanes. The mixture was condensed under reduced pressure and the crude material was purified on preparative HPLC MS using the short high pH shallow gradient method (Mobile phase: 50-70% B; A: H2O with 10 mM NH4CO3 and 0.375% NH4OH v/v, B: CH3CN, 10 min run) on XBridge Prep C18 OBD, 30x50 mm, 5 mm, Waters reverse phase column, to afford tert-butyl 4-(3-chloro-4-cyanophenyl)piperazine-1-carboxylate (0.490 g, 47.1 %) as a white solid.

Here is a chemical reaction formula: Reactants are:aryl halide:CC1=NC(=CC=C1)Br;amine:C/C=C(/C1=CC=C(C=C1)C)\N(C2=CC=C(C=C2)OC)C(=O)NC, Reagents are:Solvent:CC1=CC=CC=C1;Base:CC(C)(C)[O-].[Na+];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;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], and Products are 0:C/C=C(/C1=CC=C(C=C1)C)\N(C2=CC=C(C=C2)OC)C(=O)N(C)C3=CC=CC(=N3)C, please give me the reaction condition of this formula.

The condition of this chemical reaction is: (Z)-1-(4-methoxyphenyl)-3-methyl-1-(1-p-tolylprop-1-enyl)urea (0.17200 g, 0.55 mmol),2-bromo-6-methylpyridine (0.126 ml, 1.11 mmol),SODIUM TERT-BUTOXIDE (0.160 g, 1.66 mmol),XANTPHOS (0.032 g, 0.06 mmol) and Pd2(dba)3 (0.025 g, 0.03 mmol) were dissolved intoluene (5.42 ml) and sparged under nitrogen for 15minutes . The resulting mixture was then heated to 110 °C for 29/03/2010 48 hours or unitil conversion was complete by TLC. NH4Cl (10 mL) was added 31-Mar-10 09:49:52 +0100 and the mixture was extracted twice (EtOAc 20 mL). The organic phases were combined, washed with brine (20 mL), dried (MgSO4) and the solvent removed under reduced pressure. The crude product was then purified by flash column chromatography to give (Z)-1-(4-methoxyphenyl)-3-methyl-3-(6-methylpyridin-2-yl)-1-(1-p-tolylprop-1-enyl)urea (0.189 g, 85 %) 633-444 = 189 mg

Here is a chemical reaction formula: Reactants are:amine:CC(=O)NC1=CC(=C(C=C1C2CC2)F)N;aryl halide:C1C(CO1)NC2=CC(=NC3=C(C=NN23)C#N)Cl, Reagents are:metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C;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];Base:C(=O)([O-])[O-].[Cs+].[Cs+];Solvent:C1COCCO1, and Products are 0:CC(=O)NC1=CC(=C(C=C1C2CC2)F)NC3=NC4=C(C=NN4C(=C3)NC5COC5)C#N, please give me the reaction condition of this formula.

The condition of this chemical reaction is: dioxane (4 mL) was adde to the mixture of N-(5-amino-2-cyclopropyl-4-fluorophenyl)acetamide (100 mg, 0.48 mmol), 5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (132 mg, 0.53 mmol),cesium carbonate (469 mg, 1.44 mmol), Pd2(dba)3 (44.0 mg, 0.05 mmol), di-tert-butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (40.8 mg, 0.10 mmol) in 5 ml microwave vial. N2 flow was bubbled through for 3 mins. Then the reaction solution was sealed with cap, degassed and refilled with argon 3 times. The resulting solution was heated at 140°C for 40 mins in microwave. LC/MS showed desired product as major peak. After the crude solution was concentrated, the crude residue was purified by chromatography (100% EtOAc to 3% MeOH in EtOAc). N-(5-(3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-ylamino)-2-cyclopropyl-4-fluorophenyl)acetamide (48.4 mg, 23.91 %) was obtained.

Here is a chemical reaction formula: Reactants are:aryl halide:C1C(CO1)NC2=CC(=NC3=C(C=NN23)C#N)Cl;amine:CC(=O)NC1=CC(=C(C=C1C2CC2)F)N, Reagents are:metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C;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];Base:C(=O)([O-])[O-].[Cs+].[Cs+];Solvent:C1COCCO1, and Products are 0:CC(=O)NC1=CC(=C(C=C1C2CC2)F)NC3=NC4=C(C=NN4C(=C3)NC5COC5)C#N, please give me the reaction condition of this formula.

The condition of this chemical reaction is: The mixture of N-(5-amino-2-cyclopropyl-4-fluorophenyl)acetamide (54.2 mg, 0.26 mmol), 5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (50.0 mg, 0.20 mmol), cesium carbonate (196 mg, 0.60 mmol), Pd2(dba)3 (18.34 mg, 0.02 mmol) and di-tert-butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (17.01 mg, 0.04 mmol) sealed with microwave vial was degassed and refilled with argon 3 times. Then the degassed dioxane (4 mL) was added. The resulting solution was heated at 130°C for 30 mins in microwave. After removed all the solvents, the crude residue was purified by chromatography (100% EtOAc to 3% MeOH in EtOAc). N-(5-(3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-ylamino)-2-cyclopropyl-4-fluorophenyl)acetamide (10.00 mg, 11.85 %) was obtained.

Here is a chemical reaction formula: Reactants are:amine:CC(=O)NC1=CC(=C(C=C1C2CC2)F)N;aryl halide:C1C(CO1)NC2=CC(=NC3=C(C=NN23)C#N)Cl, Reagents are:Solvent:CC(=O)N(C)C;Base:C(=O)([O-])[O-].[Cs+].[Cs+];metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C;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], and Products are 0:CC(=O)NC1=CC(=C(C=C1C2CC2)F)NC3=NC4=C(C=NN4C(=C3)NC5COC5)C#N, please give me the reaction condition of this formula.

The condition of this chemical reaction is: In a microwave tube, was Cs2CO3 (0.522 g, 1.60 mmol), N-(5-amino-2-cyclopropyl-4-fluorophenyl)acetamide (0.167 g, 0.80 mmol), Pd2dba3 (0.037 g, 0.04 mmol),5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.200 g, 0.80 mmol),di-tert- butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.034 g, 0.08 mmol). anhydrous DMA (1.0 mL) was added. The resulting mixture was bubbled through N2. Then the tube was capped. under microwave 145C for 25min. LCMS showed product and byproduct mass, did not showed SM The mixture was filtered through celite. The resulting black solution was concentrated to dryness by rotavapor. The crude product was purified by ISCO (40g, Hex to EtOAc:HEx=1;2 to 1;1 to EtOAcO) to give product (offwhite solid). HPLC showed some impurity. This offwhite solid was washed with warm EtOAc (1mL) to giveN-(5-(3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-ylamino)-2-cyclopropyl-4-fluorophenyl)acetamide (0.012 g, 3.55 %) LCMS and NMR were OK, see attachment.

Here is a chemical reaction formula: Reactants are:amine:CC1=CSC(=N1)N;aryl halide:C1=CC(=NC(=C1)Br)C(=O)O, Reagents are:Solvent:CC1=CC=CC=C1;Base:CC(C)(C)[O-].[Na+];metal and ligand:CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C;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], and Products are 0:CC1=CSC(=N1)NC2=CC=CC(=N2)C(=O)O, please give me the reaction condition of this formula.

The condition of this chemical reaction is: _The aim of this reaction is to synthesize material to check some ideas for route development and see if 'normal' Buchwald conditions is applicable here. IPC.s were taken and the reaction was monitored either by LCMS or HNMR (a crude sample dissolved in DMSO)._ 19/11-2015 14:00 A dried 250 mL rb-flask under nitrogen atmosphere was charged with 4-methylthiazol-2-amine (C0033995, BT250061) (6.61 g, 57.92 mmol), 6-bromopicolinic acid (C0013377, BT249846) (11.7 g, 57.92 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (C0007769, BT234652) (1.326 g, 1.45 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphane (C0018897, BT153355) (2.76 g, 5.79 mmol), SODIUM T-BUTOXIDE (C0006296, BT235115) (16.70 g, 173.76 mmol), Toluene (193 ml) was added and the suspension was heated and stirred at reflux (110 °C). Start heating 14:30 - IPC was taken after 18 h **IPC1 LCMS** , seems difficult to identify if any of the desired product was formed. Made an aqueous wash between citric acid/water and ethyl acetate, tedious separation, analysed the two phases IPC2 LCMS but still impossible to identify any product neither in the organic phase IPC3 LCMS. **No evidence of product formation.** The phases were discarded and the reaction judged as failed

Here is a chemical reaction formula: Reactants are:amine:CC(C)(C)OC(=O)N1CCNCC1;aryl halide:C1=CC(=NC(=C1)Cl)C(F)(F)F, Reagents are:Solvent:CC1=CC=CC=C1;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;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];Base:CC(C)(C)[O-].[Na+], and Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC(=N2)C(F)(F)F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A 20 mL microwave vial was charged with 2-chloro-6-(trifluoromethyl)pyridine (860 mg, 4.74 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (295 mg, 0.47 mmol), Sodium tert-butoxide (546 mg, 5.68 mmol), tert-butyl piperazine-1-carboxylate (882 mg, 4.74 mmol) and a mixture of toluene (25 mL) and DMF (5 mL). The reaction mixture was degassed for 10 minutes with nitrogen, and then Tris(dibenzylideneacetone)dipalladium(0) (217 mg, 0.24 mmol) was added. The reaction mixture was stirred at 105°C in an oil bath 12h. The solution was diluted with EtOAc and washed with saturated NaHCO3 solution, brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was loaded on a 80g silica gel column and purified on a Teledyne Isco instrument, eluting with 0% to 100% ethyl acetate in heptane to provide tert-butyl 4-(6-(trifluoromethyl)pyridin-2-yl)piperazine-1-carboxylate (811 mg, 51.7 %) as a solid.

Here is a chemical reaction formula: Reactants are:amine:CC(C)(C)OC(=O)N1CCNCC1;aryl halide:C1=CC(=NC(=C1)Cl)C(F)(F)F, Reagents 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;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];Base:CC(C)(C)[O-].[Na+];Solvent:CC1=CC=CC=C1, and Products are 0:CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC(=N2)C(F)(F)F, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A 2.0-5.0 mL microwave vial was charged with 2-chloro-6-(trifluoromethyl)pyridine (86 mg, 0.47 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (29.5 mg, 0.05 mmol), Sodium tert-butoxide (54.6 mg, 0.57 mmol), tert-butyl piperazine-1-carboxylate (88 mg, 0.47 mmol) and a mixture of toluene (2.5 mL) and DMF (.5 mL). The reaction mixture was degassed for 10 minutes with nitrogen, and then Tris(dibenzylideneacetone)dipalladium(0) (21.69 mg, 0.02 mmol) was added. The reaction mixture was stirred at 105°C in an oil bath 12h. The solution was diluted with EtOAc and washed with saturated NaHCO3 solution, brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was loaded on a 24g silica gel column and purified on a Teledyne Isco instrument, eluting with 0% to 100% ethyl acetate in heptane to provide tert-butyl 4-(6-(trifluoromethyl)pyridin-2-yl)piperazine-1-carboxylate (72.8 mg, 46.4 %) as a solid.

Here is a chemical reaction formula: Reactants are:aryl halide:COC1=C(C=CC(=C1)Br)Cl;amine:CC(C)(C)OC(=O)N1CC2CNCC2C1, Reagents are:Solvent:CC1=CC=CC=C1;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;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];Base:CC(C)(C)[O-].[Na+], and Products are 0:CC(C)(C)OC(=O)N1CC2CN(CC2C1)C3=CC(=C(C=C3)Cl)OC, please give me the reaction condition of this formula.

The condition of this chemical reaction is: A mixture of tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (205 mg, 0.97 mmol), 5-Bromo-2-chloroanisole (235 mg, 1.06 mmol), Sodium tert- butoxide (130 mg, 1.35 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (30.1 mg, 0.05 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (44.2 mg, 0.05 mmol) in toluene (10 mL) under a nitrogen atmosphere was stirred at 90 °C for 12h. The solution was washed with saturated NaHCO3 solution, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was loaded on a 24g silica gel column and purified on a Teledyne Isco instrument, eluting with 20% to 40% ethyl acetate in heptane to provide tert-butyl 5-(4-chloro-3-methoxyphenyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (220 mg, 64.6 %) as a solid. Used directly for the next step. MS m/z 353.3 [M+H]+ (ESI)