HCID 86718607, compound → HCID 86718608, compound

Participants

Reaction Steps

A solution of 5-(3′-fluoro-4-((2-methoxyethoxy)methoxy)-[1,1′-biphenyl]-3-yl)-2-(trifluoromethyl)pyridine (1.61 g, 3.82 mmol) in methanol (100 mL) and 1.0 M aqueous hydrochloric acid (50 mL) was stirred at 60° C. for 2 days. The cooled reaction mixture was concentrated under reduced pressure to remove methanol, and the resulting aqueous suspension partitioned between ethyl acetate (100 mL) and saturated aqueous sodium hydrogen carbonate solution (100 mL). The organic phase was separated, washed with water (75 mL) and saturated brine (75 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give a cream solid. The crude product was purified by chromatography on silica eluting with a solvent gradient of 0 to 50% ethyl acetate (containing 2% methanol) in hexanes to give 3′-fluoro-3-(6-(trifluoromethyl)pyridin-3-yl)-[1,1′-biphenyl]-4-ol (1.04 g, 81% yield) as a white crystalline solid.

Provenance & Evidence