Tetrahydrofuran → [3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]-carbamic acid methyl ester

Participants

Reaction Steps

Into a reaction flask, {3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-carbamic acid methyl ester (5, 1.91 g, 4.63 mmol) is combined with 10 mL of tetrahydrofuran and Dess-Martin periodinane (2.36 g, 5.56 mmol). The reaction is stirred at room temperature for 2 hours, then diluted with 50 mL of 1M aqueous potassium carbonate and 50 mL of 1M aqueous sodium thiosulfate and extracted with 3×30 mL of ethyl acetate. The organic layers are combined, dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound (6, 1.91 g).

Provenance & Evidence