Ammonium Chloride → (4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)(phenyl)methanol

Participants

Reaction Steps

To a stirred solution of (4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)(phenyl)methanone (0.16 g, 0.48 mmol) in THF (1.5 mL) and ethanol (95%, 1.5 mL) was added sodium borohydride (30 mg, 0.79 mmol). The mixture was stirred at rt for 30 min before saturated ammonium chloride aqueous solution was added with caution. The mixture was concentrated and partitioned between water and ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate. Combined organic solutions were dried (Na2SO4), filtered through a pad of silica gel, and concentrated to give (4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)(phenyl)methanol (0.16 g, 0.48 mmol, 100% yield) as a yellow solid.

Provenance & Evidence