Potassium Carbonate → 2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid pyrrolo[3,2-b]pyridin-1-ylamide

Participants

Reaction Steps

A solution of 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid chloride (0.45 mmol) in EtOAc (8 mL) is added to a stirred solution of pyrrolo[3,2-b]pyridin-1-ylamine (0.45 mmol) and potassium carbonate (0.45 mmol) in EtOAc (4 mL) and H2O (8 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. The solid is purified by silica gel chromatography eluting with 20-80% EtOAc in heptane to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid pyrrolo[3,2-b]pyridin-1-ylamide (38 mg, 24%) as a solid. MS: 348 (M+H); 1H NMR (300 MHz, CDCl3): δ 2.76 (s, 3H), 6.59 (m, H) 7.07-7.64 (m, 4H), 7.96 (m, H), 8.23 (m, H), 8.32 (m, 2H), 9.12 (s, H), 10.01 (br, N—H).

Provenance & Evidence