Ethanol → 1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [1-(6-methylamino-pyridin-3-yl)-cyclopropyl]-amide

Participants

Reaction Conditions

Reaction Steps

A pressure tube charged with 1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [1-(6-bromo-pyridin-3-yl)-cyclopropyl]-amide (0.200 g, 0.442 mmol), 33% methylamine in ethanol (0.250 mL, 1.99 mmol) in N-methylformamide (1 mL) is heated at 160° C. After 36 hours, the reaction is cooled to room temperature and diluted with ethyl acetate (20 mL) and water (20 mL). Phases are separated and the aqueous layer is extracted with ethyl acetate (3×20 mL). The combined organic layers are washed with saturated aqueous ammonium chloride (3×100 mL), saturated aqueous sodium bicarbonate (100 mL), brine (100 mL), dried over MgSO4, filtered and concentrated. The residue is purified by silica gel chromatography eluting with 0-15% methanol in dichloromethane to afford the title compound as a solid.

Provenance & Evidence