Potassium Carbonate → 4-Chlorophenyl 4-(4-chloro-2-(imidazo[1,2-a]pyridin-5-yl)phenoxy)-2,5-difluorobenzenesulfonate

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Reaction Steps

To a stirred mixture of 4-chlorophenyl-2,4,5-trifluorobenzenesulfonate (1.64 g, 5.10 mmol) and potassium carbonate (2.11 g, 15.3 mmol) in dimethylsulfoxide (15 mL) at ambient temperature was added 4-chloro-2-(imidazo[1,2-a]pyridin-5-yl)phenol (1.25 g, 5.10 mmol). The mixture was stirred at ambient temperature for 3 h and diluted with ethyl acetate (50 mL) and water (20 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a 20-50% gradient of ethyl acetate in dichloromethane to afford 4-chlorophenyl 4-(4-chloro-2-(imidazo[1,2-a]pyridin-5-yl)phenoxy)-2,5-difluorobenzenesulfonate as a colorless foam in 66% yield (1.84 g): 1H NMR (300 MHz, DMSO-d6) δ7.92-7.40 (m, 10 H), 7.27 (dd, J=7.5, 7.5 Hz, 1H), 7.11-6.90 (m, 3H); MS (ES+) m/z 546.8 (M+1), 548.8 (M+1).

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