Phosphorus oxychloride → 7-Chloro-2-(trimethylsilyl)furo[3,2-b]pyridine

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Reaction Steps

A solution of 2-(trimethylsilyl)furo(3,2-b)pyridine N-oxide (32 g, 0.153 mol) in POCl3 (150 ml) is heated to 100° C. for 2 h in a sealed pressure tube. The reaction mixture is cooled to RT, concentrated under vacuum, the residue is dissolved in DCM (500 ml), washed with saturated sodium bicarbonate (100 ml×2), water (50 ml×2) and with sat brine (50 ml), dried over sodium sulphate and concentrated under vacuum. The crude material is purified by column chromatography by using petrolether/ethyl acetate (9:1) as an eluent to afford the title compound as (18 g, 52%) light brown oil. TLC: hexane/ethyl acetate: (8/2): Rf=0.80; 1H NMR (DMSO-d6, 400 MHz) δ [ppm] 8.461-8.448 (1H, d, J=5.2 Hz), 7.502-7.477 (2H, m), 0.372-0.355 (9H, s); LCMS (method C): 3.29 min (purity 95.8%), M+H+ 226.0.

Provenance & Evidence