Phosphorus oxychloride → 4-Chloro-7-iodo-2-methylthiazolo[4,5-c]pyridine

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Reaction Steps

7-Iodo-2-methyl-5H-thiazolo[4,5-c]pyridin-4-one (880 mg, 3.01 mmol) was suspended in POCl3 (8.25 ml, 90.4 mmol) and refluxed for 4 hrs. The black reaction mixture was evaporated and poured as a dichloromethane solution in ice water. The aqueous layer was neutralized with solid NaHCO3 to pH 7 and extracted three times with dichloromethane. The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude product was purified by chromatography on silica gel (dichloromethane/methanol 100:0->95:5 gradient). The desired product was obtained as a light yellow solid (280 mg, 30%), MS: m/e=311.0 (M+H+).

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