Sodium hydride → N-(2-azidopyridin-4-yl)-2,4,6-trichlorobenzamide

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of 2-azidopyridin-4-amine (500 mg, 3.7 mmol) in dry DMF (10 ml) was added NaH (178 mg, 7.4 mmol). After stirring for 10 min, a solution 2,4,6-trichlorobenzoyl chloride (1.8 g, 7.4 mmol) in DMF (5 mL) was added dropwise. The reaction was warmed to 25° C. and stirring was continued for 30 min. The reaction was diluted with water (50 mL) and extracted with ethyl acetate (3×10 mL). The combined organic extracts were washed with water (20 mL), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica-gel chromatography (petroleum ether/ethyl acetate=1:1) to afford N-(2-azidopyridin-4-yl)-2,4,6-trichlorobenzamide (180 mg, yield: 14%). LCMS (ESI) m/z: 342.0 [M+H+].

Provenance & Evidence