Pyridine → 3,5-Dichloro-4-(4-chloro-thiazolo[5,4-c]pyridine-2-yl)-benzonitrile

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Reaction Steps

A mixture of 2,6-dichloro-N-(2-chloro-3-fluoro-pyridin-4-yl)-4-cyano-benzimidoyl chloride (454 mg, 1.25 mmol), thiourea (380 mg, 5.0 mmol) and pyridine (325 μL, 4.0 mmol) in anhydrous isopropanol (4 mL) was heated under reflux, under nitrogen, for 16 hours. Triethylamine (1.05 mL, 7.5 mmol) was added and the resultant mixture was heated under reflux for a further 6.5 hours. The mixture was cooled to ambient temperature and concentrated to dryness under reduced pressure. The residue was partitioned between DCM (15 mL) and water (15 mL). The aqueous phase was extracted with DCM (2×10 mL) and the combined organic extract was dried over MgSO4 and concentrated to dryness under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0-20% EtOAc in DCM. The resultant solid was triturated with cyclohexane and dried under reduced pressure to give the desired compound as a white solid (275 mg, 65% yield). 1H NMR (400 MHz, CDCl3): δ 8.55 (d, J=5.6 Hz, 1H), 8.00 (d, J=5.6 Hz, 1H), 7.79 (s, 2H).

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