Potassium Carbonate → 4-methoxy-2-[4-(trifluoromethyl)phenyl]-5-[[3-(trifluoromethyl)-1H-pyrazol-1-yl]methyl]-2H-1,2,3-triazole

Temperature

55 °C

To a solution of 4-(bromomethyl)-5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole (i.e. the product of Example 1, Step D) (0.25 g, 66 weight %, 0.5 mmol) in N,N-dimethylformamide (2 mL total), was added 3-(trifluoromethyl)pyrazole (0.082 g, 0.6 mmol) and anhydrous potassium carbonate (0.21 g, 1.5 mmol). The mixture was heated to 55° C. and stirred for 75 min. The reaction mixture was cooled to 23° C., diluted with water (20 mL) and extracted with ethyl acetate (15 mL). The organic layer was washed with water (10 mL) and saturated aqueous sodium chloride solution (10 mL), dried (MgSO4) and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel eluting with 0 to 40% ethyl acetate in hexanes to afford the title compound (0.098 g) as a colorless oil.

1. temperatureThe reaction mixture was cooled to 23° C.
2. extractionextracted with ethyl acetate (15 mL)
3. washThe organic layer was washed with water (10 mL) and saturated aqueous sodium chloride solution (10 mL)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated under reduced pressure
6. customThe crude residue was purified by chromatography on silica gel eluting with 0 to 40% ethyl acetate in hexanes

ORD record

ord-ae61bf80c1e041cc8f1c8cb13d60d106

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09302999B2