Sodium hydride → N-(3-bromopyridin-2-ylmethyl)-4-fluoro-benzamide

Participants

Reaction Steps

To a mixture of 3-bromo-2-bromomethyl-pyridine (1.30 g, 5.18 mmol) and 4-fluoro-benzamide (725 mg, 5.21 mmol) in THF (20 mL) is added 60% sodium hydride in mineral oil (210 mg, 5.3 mmol) and the mixture is warmed at reflux. After 24 hours, the mixture is diluted with saturated aqueous ammonium chloride (25 mL) and extracted with ethyl acetate (2×25 mL). The combined organic layers are washed with brine (2×25 mL), dried over magnesium sulfate, filtered and concentrated. The residue is purified by silica gel chromatography eluting using a gradient of 5-25% EtOAc in hexanes to afford N-(3-bromopyridin-2-ylmethyl)-4-fluoro-benzamide.

Provenance & Evidence