Pyridine → HCID 86669015, compound

Participants

Reaction Steps

A stirred solution of 2-bromo-6-chloro-N-(2-chloro-3-fluoropyridin-4-yl)-benzimidoyl chloride (4.2 g, 11.0 mmol), thiourea (2.5 g, 33.0 mmol) and pyridine (3.1 mL, 38.4 mmol) in isopropanol (50 mL) under a nitrogen atmosphere was heated under reflux for 3 hours. Et3N (7.6 mL, 54.6 mmol) was added and the reaction mixture was heated under reflux for 1.5 hours. After cooling to room temperature, the volatiles were removed under reduced pressure. The resultant residue was triturated with water (100 mL) and then boiled in isopropanol (15 mL) for 10 minutes. After cooling to room temperature, the resultant solid was collected by filtration and then purified by column chromatography on silica gel eluting with 25% diethyl ether in pentane to afford the title compound as a colourless solid (2.1 g, 53%). LCMS (Method E): RT=4.16 min, m/z: 361 [M+H+].

Provenance & Evidence