Methyl iodide → tert-Butyl (4-bromopyridin-2-yl)(methyl)carbamate

Participants

Reaction Steps

To a solution of tert-butyl carbamate 155 (300 mg, 1.10 mmol) in THF (5 mL) at 0° C. is added sodium hydride (53 mg, 1.32 mmol, 60% dispersion in mineral oil) in one portion. After stirring 15 minutes, iodomethane is added (82 μL, 1.32 mmol) and the reaction mixture warmed to RT and stirred 16 h. The reaction is then quenched with 5% citric acid (10 mL) and extracted into EtOAc (2×10 mL). The combined organic phases are dried over Na2SO4 and purified by column chromatography (70% EtOAc in heptane) to give the title compound.

Provenance & Evidence