Potassium Carbonate → 3-(3-Bromo-4-methylphenyl)-1-[3-(trifluoromethyl)phenyl]-1h-pyrazole

HRID 70251

Reaction equation

HRID 70251 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[CH:12][NH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].I[C:15]1[CH:16]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(OCC)(=O)C.[Cu]I.N[C@@H]1CCCC[C@H]1N>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[CH:12][N:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

9

Reactant 3

HCID 11430Potassium CarbonateHCID 67868Benzene, 1-iodo-3-(trifluoromethyl)-HCID 178423828HCID 178423828, compound2×

Product 1

HCID 667897643-(3-Bromo-4-methylphenyl)-1-[3-(trifluoromethyl)phenyl]-1h-pyrazole

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 438061,2-Diaminocyclohexane, trans-CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 3-(3-bromo-4-methylphenyl)-1H-pyrazole (i.e. the product of Step B) (5.0 g, 21.09 mmol) in p-dioxane (19 mL) under a nitrogen atmosphere was added 3-iodobenzotrifluoride (5.75 g, 21.11 mmol), copper(I) iodide (0.05 g, 0.262 mmol), trans-1,2-diaminocyclohexane (253.5 μL, 2.10 mmol) and potassium carbonate (6.1 g, 44.14 mmol). The reaction mixture was heated at 100° C. overnight, cooled to room temperature and diluted with water and ethyl acetate. The resulting mixture was separated, and the aqueous layer was extracted with ethyl acetate (3×). The combined organic layers were washed with hydrochloric acid (1N), saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide a solid (9 g). Hexanes were added to the solid, and the mixture was filtered to obtain the title compound as a solid (6.4 g).

Workup

  1. temperaturecooled to room temperature
  2. customThe resulting mixture was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×)
  4. washThe combined organic layers were washed with hydrochloric acid (1N), saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ffe904866334572985715c6e26116d9
Source dataset
uspto-grants-2014_09
Patent number
US08822521B2

Linked notes

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