Thionyl Chloride → 6-(Chloromethyl)-2-(methylthio)thiazolo[4,5-b]pyridine

Participants

Reaction Steps

To a stirred mixture of (2-(methylthio)thiazolo[4,5-b]pyridin-6-yl)methanol (404 mg, 2 mmol) in anhydrous CH2Cl2 (20 mL) at rt was added SOCl2 (166 μL, 2.4 mmol). After 3 h, the mixture was concentrated under reduced pressure to afford 6-(chloromethyl)-2-(methylthio)thiazolo[4,5-b]pyridine (497 mg) as a white solid. The material was used in the next step without further purification. 1H NMR (300 MHz, DMSO-d6) δ 8.65 (d, J=1.9 Hz, 1H), 8.60 (d, J=1.9 Hz, 1H), 4.95 (s, 2H), 2.83 (s, 3H); LCMS (ESI) m/z 231 (M+H)+.

Provenance & Evidence