Potassium Carbonate → tert-Butyl 4-{4-[4-(2-chloro-4-{[(2,4-dimethoxybenzyl)(1,3,4-thiadiazol-2-yl)amino]sulfonyl}-5-fluorophenoxy)-4'-(trifluoromethyl)biphenyl-3-yl]pyridin-2-yl}piperazine-1-carboxylate

Participants

Reaction Steps

tert-Butyl 4-(4-(4-hydroxy-4′-(trifluoromethyl)biphenyl-3-yl)pyridin-2-yl)piperazine-1-carboxylate (Preparation 114, 200 mg, 0.400 mmol) was dissolved in dimethyl sulfoxide (3 mL) and potassium carbonate (110 mg, 0.800 mmol) was added followed by 5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide (Preparation 16, 185 mg, 0.400 mmol). The reaction was stirred at room temperature for 18 hours and then partitioned between ethyl acetate (10 mL) and water (5 mL). The organic layer was separated and washed with brine (5 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified on silica gel by Biotage™ (7% to 60% ethyl acetate in heptane over 20 CV) to give the title product (340 mg, 90%) as a yellow foam.

Provenance & Evidence