Pyridine → 3,5-Dichloro-4-(7-fluorothiazolo[5,4-c]pyridin-2-yl)-benzonitrile

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of 2,6-dichloro-4-cyano-N-(3,5-difluoropyridin-4-yl)-benzimidoyl chloride (1.5 g, 4.33 mmol), thiourea (1.32 g, 17.34 mmol) and pyridine (1.19 mL, 14.72 mmol) in isopropanol (13 mL) under a nitrogen atmosphere was heated at 90° C. for 4 hours. After cooling to 60° C., Et3N (3.62 mL, 25.98 mmol) was added and heating at 85° C. was continued for 18 hours, then at 90° C. for a further 18 hours. After cooling to room temperature, the volatiles were removed under reduced pressure and the resultant residue was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc (×2) and the combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with 0-90% EtOAc in cyclohexane to afford the title compound as a yellow solid (417 mg, 30%). LCMS (Method D): RT=3.53 min, m/z: 324 [M+H+].

Provenance & Evidence