Methyl iodide → 5-bromo-2-(methoxymethyl)Pyridine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-bromo-2-(hydroxymethyl)pyridine (150 mg, 0.798 mmol) in THF (8 mL) under nitrogen at r.t. was added sodium hydride (60% dispersion in oil, 64 mg, 1.60 mmol). After 30 minutes iodomethane was added and the reaction mixture was heated to 60° C. for 3 h, then cooled to r.t. and concentrated in vacuo. The residue was partitioned between DCM (50 mL) and water (50 mL); the organic fraction was washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo to give the title compound (70 mg, 65%) as 70% pure material. LCMS (ES+) 202.0 (M+H)+, RT 2.40 minutes (Method 1).

Provenance & Evidence