Hydrochloric Acid → 5-Chloro-2-fluoro-N-(5-fluoropyridin-2-yl)-4-{[3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-yl]oxy}benzenesulfonamide

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Reaction Steps

5-Chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamide (Preparation 105, 23 mg, 0.04 mmol), 3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-ol (Preparation 107, 9 mg, 0.04 mmol) and potassium carbonate (15 mg, 0.11 mmol) in dimethyl sulfoxide (1 mL) were stirred at room temperature for 2 hours. The mixture was treated with aqueous 2M HCl (3 mL). The resulting mixture was extracted with dichloromethane (3 mL). The dichloromethane layer was dried through a phase separating cartridge followed by treatment with trifluoroacetic acid (500 μL). The mixture was stirred for 2 hours and allowed to stand at room temperature for 18 hours. The mixture was then treated with a saturated solution of ammonium chloride (5 mL). The dichloromethane layer was separated, dried through a phase separating cartridge and evaporated in vacuo. The residue was purified by preparative HPLC to afford the title compound (14 mg, 45%).

Provenance & Evidence