4-Toluenesulfonyl chloride → N-(5-fluoropyridin-2-yl)-4-methylbenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

2-amino-5-fluoropyridine (25 g, 0.22 mol) in pyridine (100 mL) was treated portion wise with p-toluenesulfonyl chloride (47.5 g, 0.25 mol) and heated at 80° C. for 2 hours. The cooled material was concentrated to remove the majority of pyridine. The resulting viscous solution was diluted with 200 ml of ethyl acetate then 200 ml of water. The resulting suspension was stirred for about an hour to break up the solids then filtered. The filter cake was washed with water then cold ethyl acetate, dried to afford 59 g of a light brown solid. Rf 0.43, 50% ethyl acetate/hexanes; MS m/z 266 (M+H).

Provenance & Evidence