Acetic Acid → N-((5-bromopyridin-3-yl)methyl)ethanesulfonamide

Participants

Reaction Steps

To a solution of 5-bromo-3-pyridinecarboxaldehyde (CAS#113118-81-3, 450 mg, 2.4 mmol) in dichloroethane (15 mL) was added ethanesulfonamide (CAS#1520-70-3, 175 mg, 1.6 mmol), acetic acid (0.18 mL 3.2 mmol), triethylamine (0.45 mL, 3.2 mmol) and sodium triacetoxyborohydride (1.0 g, 4.8 mmol). The reaction was stirred at room temperature for 3 hours, at which time it was diluted with dichloromethane and saturated aqueous sodium bicarbonate. The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 10 to 100%) to provide ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-amide; MS: (ES+) m/z 278.9 (M+H)+.

Provenance & Evidence