Potassium Carbonate → N-(5-bromo-2-chloropyridin-3-yl)-3-(difluoromethoxy)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A round bottomed flask was charged with 3-amino-5-bromo-2-chloropyridine (1.5 g, 7 mmol, Asymchem Laboratories, Inc. Morrisville, N.C.) and pyridine (20 mL). To this solution, 3-(difluoromethoxy)benzenesulfonyl chloride (2 mL, 8 mmol, Sigma-Aldrich Corporation, St. Louis, Mo.) was added dropwise and the solution was stirred at 25° C. for 18 h. The mixture was concentrated in vacuum and the residue was suspended in H2O. The white solid was collected by filtration and then suspended in methanol (50 mL). To this suspension, potassium carbonate (1.9 g, 14 mmol) was added, and the mixture was stirred at 25° C. for 20 h. The suspension was filtered and the filtrate was concentrated in vacuo. Purification by silica gel chromatography (10-50% EtOAC/Hexane) afforded the title compound (1.4 g, 47% yield) as a white solid. MS (ESI positive ion) m/z: 415 (M+1).

Provenance & Evidence