Pyridine → 4-Chloro-2-(2,6-dichloro-4-iodophenyl)thiazolo[5,4-c]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,6-dichloro-N-(2-chloro-3-fluoropyridin-4-yl)-4-iodobenzimidoyl chloride (2.94 g, 6.30 mmol), thiourea (1.93 g, 25.3 mmol) and pyridine (1.73 mL, 21.4 mmol) in isopropanol (25 mL) was heated to 90° C. for 3.5 hours. Triethylamine (5.3 mL, 37.8 mmol) was added and the resulting mixture was heated to 90° C. for a further 1.5 h. The reaction was cooled to room temperature and then concentrated under reduced pressure. The resultant residue was partitioned between DCM and water. The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure. The residue was triturated with MeOH and dried under reduced pressure to give the desired compound (2.33 g, 84% yield). 1H NMR (300 MHz, CDCl3): δ 8.52 (d, J=5.6 Hz, 1H), 7.98 (d, J=5.6 Hz, 1H), 7.90-7.81 (s, 2H).

Provenance & Evidence