Potassium Carbonate → 5-Chloro-4-(6-chloro-3'-fluoro-4-(pyridazin-4-yl)biphenyl-3-yloxy)-N-(2,4-dimethoxybenzyl)-2-fluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide

Participants

Reaction Steps

5-Chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide (Preparation 16, 136 mg, 0.29 mmol) was added to a solution of 6-chloro-3′-fluoro-4-(pyridazin-4-yl)biphenyl-3-ol (Preparation 98, 133 mg, 0.29 mmol) and potassium carbonate (183 mg, 0.88 mmol) in dimethylsulfoxide (5 mL). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with sodium hydroxide (1M, 5 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in dimethylsulfoxide:acetonitrile (2.5 mL: 1.5 mL) and then purified on the reverse phase HPLC eluting with acetonitrile:water (from 5:95 to 95:5, 30 minutes gradient then 5 minutes isocratic) to give the title compound (60 mg, 18%) as a white solid.

Provenance & Evidence