Sodium borohydride → 5-(Hydroxymethyl)-N,N-dimethylfuro[2,3-b]pyridine-2-carboxamide

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Reaction Conditions

Reaction Steps

Sodium borohydride (6.0 g, 0.16 mol) was added to a solution of 5-formyl-N,N-dimethylfuro[2,3-b]pyridine-2-carboxamide (6.9 g, 0.032 mol) in methanol (80 mL) and THF (20 mL) at 0° C., and the resulting mixture was gradually warmed to 23° C. and stirred for 1 h. The excess of sodium borohydride was carefully quenched with water. The reaction mixture was concentrated, and then 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 silica gel eluting with 70% ethyl acetate in petroleum ether to give the title compound. MS: m/z=221.0 (M+1).

Provenance & Evidence