Water → 1H-Pyrrolo[2,3-b]pyridin-5-ol

Participants

Reaction Conditions

Reaction Steps

Boron tribromide (0.506 μl, 5.35 mmol) in methylene chloride (1 ml) was added to a solution of 5-methoxy-7-azaindole (0.36 g, 2.43 mmol) in methylene chloride (25 ml) cooled at −30° C. The mixture was left to warm up to ambient temperature and was stirred overnight. The mixture was poured onto ice and water and the pH of the aqueous phase was adjusted to 6. The organic phase was separated and the aqueous phase was further extracted with ethyl acetate. The organic phases were combined, washed with brine, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography eluting with increasingly polar mixtures of methylene chloride and methanol to give 5-hydroxy-7-azaindole (0.23 g, 71%).

Provenance & Evidence