Water → 4-{[3-(5-Amino-1H-pyrazol-4-yl)-3'-cyanobiphenyl-4-yl]oxy}-5-chloro-2-fluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

5-Chloro-4-(3′-cyano-3-(3-nitro-1H-pyrazol-4-yl)biphenyl-4-yloxy)-2-fluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide (Preparation 62, 51 mg, 0.0853 mmol) was dissolved in acetonitrile (1 mL) and heated at 50° C. Potassium carbonate (58.8 mg, 0.426 mmol) followed by sodium dithionite (59.4 mg, 0.341 mmol) and water (1 mL) were added. The reaction mixture was heated at 50° C. for 2 hours, cooled to room temperature and partitioned between EtOAc (10 mL) and water (5 mL). The aqueous phase was separated and extracted with EtOAc (2×3 mL) and the combined organic phases were washed with a saturated solution of brine (3 mL), dried over MgSO4 and concentrated in vacuo. The crude residue was purified by reverse phase HPLC.

Provenance & Evidence