Potassium Carbonate → HCID 25099830, compound

HRID 2382008Notes

Reaction equation

HRID 2382008 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14](Cl)=[O:15])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[F:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[N:23]([NH2:27])[CH:22]=[CH:21]2.C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O.O>[F:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[N:23]([NH:27][C:14]([C:11]1[CH:10]=[N:9][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:13][CH:12]=1)=[O:15])[CH:22]=[CH:21]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 45078690HCID 45078690, compoundHCID 874965532-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride

Product 1

HCID 25099830HCID 25099830, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride (1 mmol) in EtOAc (20 mL) is added to a stirred solution of 5-fluoro-indol-1-ylamine (1 mmol) and potassium carbonate (1 mmol) in EtOAc (10 mL) and H2O (20 mL) at rt and the reaction mixture is stirred at rt overnight. EtOAc is evaporated in vacuo, and the resulting solid is collected by filtration to afford 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-fluoro-indol-1-yl)-amide (148 mg, 42%) as a solid. MS: 351 (M+H); 1H NMR (300 MHz, CDCl3): δ 6.56 (m, H) 7.02 (m, H), 7.12-7.34 (m, 3H), 7.51 (m, H), 8.24 (d, H), 8.34 (s, H), 8.92 (br, H), 9.24 (br, 2H).

Workup

  1. customEtOAc is evaporated in vacuo
  2. filtrationthe resulting solid is collected by filtration

Sources & evidence

ORD record
ord-6130acf6e43349deb9808509dde3d5aa
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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