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

HRID 623691Notes

Reaction equation

HRID 623691 reaction equation
Br[CH2:2][C:3]1[C:7]([O:8][CH3:9])=[N:6][N:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[N:4]=1.[F:20][C:21]([F:28])([F:27])[C:22]1[CH:26]=[CH:25][NH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:9][O:8][C:7]1[C:3]([CH2:2][N:24]2[CH:25]=[CH:26][C:22]([C:21]([F:28])([F:27])[F:20])=[N:23]2)=[N:4][N:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[N:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18070343-(Trifluoromethyl)pyrazoleHCID 901093144-(bromomethyl)-5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole2×

Product 1

HCID 901099154-methoxy-2-[4-(trifluoromethyl)phenyl]-5-[[3-(trifluoromethyl)-1H-pyrazol-1-yl]methyl]-2H-1,2,3-triazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ae61bf80c1e041cc8f1c8cb13d60d106
Source dataset
uspto-grants-2016_04
Patent number
US09302999B2

Reaction notes

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