Potassium Phosphate, Tribasic → 4-[[5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine

To a solution of 4-(bromomethyl)-5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole (i.e. the product of Step D, 0.525 g, 66 weight %, 1.0 mmol) in tetrahydrofuran/water (3:1, 4 mL total), was added tetrakis(triphenylphosphine)palladium(0) (0.059 g, 0.05 mmol), potassium phosphate tribasic (0.43 g, 2.0 mmol) and 2-(trifluoromethyl)pyridine-4-boronic acid pinacol ester (0.42 g, 1.5 mmol). The mixture was heated to reflux and stirred for 17 h. The reaction mixture was diluted with water (20 mL) and extracted twice with ethyl acetate (25 mL, 15 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel eluting with 10% ethyl acetate in hexanes to afford the title compound (0.12 g) as a pale yellow solid.

1. temperatureThe mixture was heated
2. temperatureto reflux
3. extractionextracted twice with ethyl acetate (25 mL, 15 mL)
4. dry with materialThe organic layer was dried (MgSO4)
5. concentrationconcentrated under reduced pressure
6. customThe crude residue was purified by chromatography on silica gel eluting with 10% ethyl acetate in hexanes

ORD record

ord-0279a058701e484a924658a90a89f683

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09302999B2