Potassium Carbonate → 2-[3-(3-chloro-5-cyano-phenoxy)-2-oxo-4-(trifluoromethyl)-1-pyridyl]-N-(2-chloro-4-sulfamoyl-phenyl)acetamide

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Reaction Steps

To 3-chloro-5-{[2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl]oxy}benzonitrile (3C, 0.050 g, 0.159 mmol) and potassium carbonate (0.022 g, 0.159 mmol) suspended in dimethylformamide (1 mL) was added N-[4-(aminosulfonyl)-2-chlorophenyl]-2-bromoacetamide (0.052 g, 0.149 mmol) as a solution in dimethylformamide (1 mL). The reaction mixture was allowed to stir at room temperature. After 16 hours, the reaction mixture was diluted with ethyl acetate (20 mL), washed with water (3×10 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on a pre-packed silica gel Redi Sep 12 gram column, eluting with 0-5% methanol in CH2Cl2 to yield the title compound. 1H NMR (DMSO-d6) δ 10.23 (s, 1H), 8.05-7.96 (m, 2H), 7.89 (d, J=2.1 Hz, 1H), 7.76-7.72 (m, 2H), 7.55-7.53 (m, 1H), 7.52-7.50 (m, 1H), 7.45 (s, 2H), 6.68 (d, 0.1=7.1 Hz, 1H), 5.02 (s, 2H). HRMS (M+1)=560.998.

Provenance & Evidence