1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-(4-bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (2-vinyloxyethoxy)-amide

Participants

Reaction Steps

To a solution of 6-(4-bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (1.00 equivalent) and HOBt (1.50 equivalents) is added EDCI (1.50 equivalents) at room temperature. After stirring for 1 hour, O-(2-vinyloxy-ethyl)-hydroxylamine (1.10 equivalents) and TEA (1.20 equivalents) are added. The reaction mixture is stirred for 1 hour and diluted with EtOAc. The resulting mixture is washed with saturated aqueous NH4Cl, brine, saturated aqueous NaHCO3, and brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo to give the crude material that is used directly without further purification.

Provenance & Evidence