Methanesulfonamide → 5-Chloro-4-[(5-chloro-6-fluoropyridin-3-yl)oxy]-2-fluoro-N-(methylsulfonyl)benzamide

Participants

Reaction Steps

5-Chloro-4-(5-chloro-6-fluoropyridin-3-yloxy)-2-fluorobenzoic acid (Preparation 162, 6.100 g, 19.60 mmol), 4-dimethylaminopyridine (2.330 g, 19.06 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (5.480 g, 28.59 mmol) and methanesulfonamide (2.720 g, 28.59 mmol) were suspended in DCM (20 mL). The reaction mixture was stirred at room temperature for 18 hours, quenched with aqueous 1M HCl and extracted with EtOAc. Combined organics were concentrated in vacuo. The resulting residue was purified by reverse phase chromatography to afford the title compound as a white solid (4.50 g):

Provenance & Evidence