Ethyl Acetate → HCID 178526795, compound

Participants

Reaction Steps

BBr3 (7.4 mL, 7.4 mmol, 1M in heptane) was added to a solution of 3-(benzyloxymethyl)-5-nitro-1H-pyrazolo[3,4-b]pyridine (0.70 g, 2.46 mmol) in dichloromethane (25 mL) at −78° C., and the reaction mixture was stirred at this temperature for 1 hour. Saturated aqueous NaHCO3 was added, followed by addition of ethyl acetate. The layers were separated, and the aqueous layer extracted with ethyl acetate (2×). The combined organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography to afford (5-nitro-1H-pyrazolo[3,4-b]pyridin-3-yl)methanol (417 mg, 87%), as a solid.

Provenance & Evidence