Potassium Carbonate → N-[3-Fluoro-4-({1-[(4-methylphenyl)sulfonyl]-3-vinyl-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]acetamide

Participants

Reaction Conditions

Reaction Steps

1.00 g (1.93 mmol) of N-[4-({3-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3-fluorophenyl]acetamide and 800 mg (5.79 mmol) of potassium carbonate are suspended in DMF (6 ml). The solution is degassed and vented with argon. 79 mg (0.110 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride/methylene dichloride complex and 0.85 ml (3.86 mmol) of di-n-butyl vinylboronate are then added, and the mixture is stirred at 90° C. for 3 hours. After addition of sodium bicarbonate solution, the mixture is extracted three times with dichloromethane. The combined organic phases are concentrated, and the crude product is purified by chromatography on silica gel (mobile phase: dichloromethane/acetone 20:1 to 10:1).

Provenance & Evidence