Water → α-Methyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-2-methanol

Participants

Reaction Steps

Sodium tetrahydroborate (0.15 g, 4.10 mmol) was added to a solution of 1-(5-nitro-1H-pyrrolo[2,3-b]pyridin-2-yl)ethanone (0.28 g, 1.37 mmol) in THF (8.7 mL) and methanol (0.90 mL) at 0° C., after which the reaction mixture was warmed up to room temperature and stirred for 1 hour. The reaction mixture was then treated with water and ethyl acetate, and the layers were separated. The aqueous layer was extracted once with ethyl acetate. The organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography to afford 1-(5-nitro-1H-pyrrolo[2,3-b]pyridin-2-yl)ethanol (0.12 g, 41%).

Provenance & Evidence