2-Fluoroaniline → 7-fluoro-6-(2-fluorophenylamino)-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid methyl ester (1.00 equivalent), 2-fluoroaniline (1.00 equivalent), Pd(OAc)2 (0.10 equivalents), rac-BINAP (0.15 equivalents), and Cs2CO3 (1.50 equivalents) in toluene in a sealed tube is stirred at 80° C. for 16 hours. The reaction mixture is cooled to room temperature and diluted with EtOAc. The resulting precipitate is filtered off and washed with EtOAc. The filtrate is diluted with EtOAc and washed with water. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo to give the crude material that is purified by trituration or flash column chromatography to afford the desired product.

Provenance & Evidence