Sodium hydride → 5-(((4-Methoxybenzyl)-oxy)-methyl)-N,N-dimethylfuro[2,3-b]pyridine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

An ice-cold solution of 5-(hydroxymethyl)-N,N-dimethylfuro[2,3-b]pyridine-2-carboxamide (4.2 g, 0.019 mol) in DMF (15 mL) was added dropwise to a suspension of sodium hydride (60% dispersion in mineral oil, 1.14 g, 0.0286 mol) in DMF (15 mL) at 0° C. After the resulting mixture was stirred at 0° C. for 15 min, 4-methoxybenzyl chloride (3.89 g, 286 mmol) was added. The reaction mixture was gradually warmed to 23° C., and stirred for 1 h. The excess of sodium hydride was carefully quenched with water (15 mL). The reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by flash chromatography on silcia gel eluting with 35% ethyl acetate in petroleum ether to give the title compound. MS: m/z=341.2 (M+1).

Provenance & Evidence