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

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Reaction Conditions

Reaction Steps

To a stirred solution of 2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridin-4(5H)-one (0.32 g, 1.1 mmol) in CH3CN (50 ml) was added POBr3 (0.918 g, 3.21 mmol). The mixture was heated at 100° C. for 2 hours. The mixture was cooled to room temperature, quenched with ice (200 mL) and extracted with EtOAc (3×20 mL). The combined organic extract was washed with saturated NaHCO3 (100 mL) and brine (100 mL), dried over Na2SO4, and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with a 0-10% gradient of EtOAc/petroleum ether to give the desired product as a white solid (0.22 g, 56% yield). 1H NMR (500 MHz DMSO-d6): δ 8.59 (d, J=5.5 Hz, 1H), 8.26 (d, J=6.0 Hz, 1H), 7.76-7.74 (m, 2H), 7.71-7.68 (m, 1H). LCMS (ESI) m/z: 359.1 [M+H+].

Provenance & Evidence