HCID 86718607, compound → HCID 86718608, compound

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.

1. customThe cooled reaction mixture
2. concentrationwas concentrated under reduced pressure
3. customto remove methanol
4. customthe resulting aqueous suspension partitioned between ethyl acetate (100 mL) and saturated aqueous sodium hydrogen carbonate solution (100 mL)
5. customThe organic phase was separated
6. washwashed with water (75 mL) and saturated brine (75 mL)
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customto give a cream solid
11. customThe crude product was purified by chromatography on silica eluting with a solvent gradient of 0 to 50% ethyl acetate (containing 2% methanol) in hexanes

ORD record

ord-5ba865a85ee44605a72a9c331907f2ef

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409893B2