Thionyl Chloride → 2-(2-Chloromethyl-furo[3,2-b]pyridin-6-yloxy)-thiazolo[4,5-b]pyridine

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To a suspension of [6-(thiazolo[4,5-b]pyridin-2-yloxy)-furo[3,2-b]pyridin-2-yl]-methanol (50 mg, 0.17 mmol) in DCM (1.6 mL) was added thionyl chloride (0.020 mL, 0.25 mmol). After 5 min, more thionyl chloride (0.020 mL, 0.25 mmol) was added to the suspension. After 2 h, additional thionyl chloride (0.020 mL, 0.25 mmol) was added. The solution was stirred (rt, 16 h) and concentrated to remove all volatiles to provide the product as a beige solid (53 mg, 99%). MS (ESI): mass calcd. for C14H8ClN3O2S, 317.00; m/z found, 317.9 [M+H]+.

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