Cesium carbonate → [6-(Thiazolo[4,5-b]pyridin-2-yloxy)-furo[3,2-b]pyridin-2-yl]-methanol

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Reaction Steps

To a mixture of 2-(hydroxymethyl)furo[3,2-b]pyridin-6-ol (200 mg, 1.21 mmol), 2-chloro-thiazolo-[4,5-b]pyridine hydrochloride (300 mg, 1.45 mmol) and Cs2CO3 (800 mg, 2.46 mmol) was added DMF (12 mL). The suspension was stirred (rt, 16 h) and then poured into ice-cold sat'd. aq. NH4Cl. The resultant precipitate was filtered, rinsed with water and dried to provide the product as a beige solid (326 mg, 90%). MS (ESI): mass calcd. for C14H9N3O3S, 299.04; m/z found, 300.0 [M+H]+. 1H NMR (600 MHz, CD3OD): 8.63 (d, J=2.3, 1H), 8.49 (dd, J=4.9, 1.6, 1H), 8.36 (dd, J=8.0, 1.6, 1H), 8.23 (dd, J=2.3, 0.9, 1H), 7.37 (dd, J=8.0, 4.9, 1H), 6.95 (s, 1H), 4.76 (s, 2H).

Provenance & Evidence