Pyridine → HCID 66801290, compound

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of 2-chloro-N-(3,5-difluoropyridin-4-yl)-6-fluorobenzimidoyl chloride (12.0 g, 39.4 mmol), thiourea (9.0 g, 118 mmol) and pyridine (12.7 mL, 198 mmol) in isopropanol (200 mL) was heated at 150° C. for 3.5 hours. After stirring for one additional hour, the resulting precipitate was collected by filtration. The filtrate was treated with Et3N (27 mL, 0.197 mol) and heating was continued at 150° C. for 18 hours. After cooling to room temperature, the volatiles were removed under reduced pressure and the resultant residue was partitioned between EtOAc (300 mL) and water (500 mL). The aqueous phase was extracted with EtOAc (2×300 mL) and the combined organic layers were dried and concentrated under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with 0-100% Et2O in petroleum ether and then triturated with a mixture 3:1 diethyl ether:pentane (25 mL) to afford the title compound as a cream coloured solid (4.6 g, 41%). LCMS (Method F): RT=3.39 min, m/z: 283 [M+H+].

Provenance & Evidence