Sodium hydride → 2-bromo-5-(((1R)-2,2-difluorocyclopropyl)methoxy)-4-methylpyridine

Participants

Reaction Steps

To a solution of 6-bromo-4-methylpyridin-3-ol (0.50 g) and ((1R)-2,2-difluorocyclopropyl)methyl 4-nitrobenzenesulfonate (1.077 g) in DMF (50 mL) was added sodium hydride (60% in oil, 0.106 g) under ice-cooling, and the mixture was stirred for 15 hr. The reaction mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, and the mixture was washed with saturated brine. The obtained organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.35 g).

Provenance & Evidence