Phosphorus oxybromide → 4-Bromo-2-(2-chloro-6-fluorophenyl)thiazolo[5,4-c]pyridine

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Reaction Conditions

Reaction Steps

To a stirred solution of 2-(2-chloro-6-fluorophenyl)thiazolo[5,4-c]pyridin-4(5H)-one (0.30 g, 1.1 mmol) in MeCN (50 mL), was added POBr3 (0.92 g, 3.2 mmol). The mixture was heated at 100° C. for 2 hours and then cooled to room temperature. The reaction was quenched with ice and extracted with EtOAc (3×20 mL). The combined organic extract was washed with saturated NaHCO3 solution (100 mL) and brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with a 0-10% gradient of EtOAc in petroleum ether to give the desired product as a white solid (0.22 g, 60% yield). 1H NMR (500 MHz, DMSO-d6): δ 8.59 (d, J=5.5 Hz, 1H), 8.27 (d, J=5.5 Hz, 1H), 7.76-7.68 (m, 3H). LCMS (ESI) m/z: 342.9 [M+H+].

Provenance & Evidence