Potassium Carbonate → methyl 4-((4,4,4-trifluoro-1-(4-(3-isopropyl-1H-pyrazol-1-yl)-2-methylphenyl)butyl)amino)benzoate

HRID 1520276Notes

Reaction equation

HRID 1520276 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)[CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[C:4]([CH3:26])[CH:3]=1.[CH:27]([C:30]1[CH:34]=[CH:33][NH:32][N:31]=1)([CH3:29])[CH3:28].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.O.C1(C)C=CC=CC=1>[F:12][C:11]([F:14])([F:13])[CH2:10][CH2:9][CH:8]([NH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)[C:5]1[CH:6]=[CH:7][C:2]([N:32]2[CH:33]=[CH:34][C:30]([CH:27]([CH3:29])[CH3:28])=[N:31]2)=[CH:3][C:4]=1[CH3:26]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 117840148Methyl 4-((1-(4-bromo-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoateHCID 178439403HCID 178439403, compound

Product 1

HCID 117840775methyl 4-((4,4,4-trifluoro-1-(4-(3-isopropyl-1H-pyrazol-1-yl)-2-methylphenyl)butyl)amino)benzoateYield 74%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Under a nitrogen atmosphere, a mixture of methyl 4-((1-(4-bromo-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoate (racemate) (400 mg), 3-isopropylpyrazole (154 mg), copper(I) iodide (212 mg), trans-N,N′-dimethylcyclohexane-1,2-diamine (0.352 mL), potassium carbonate (385 mg) and toluene (1.8 mL) was stirred at 110° C. overnight, water was added at room temperature, and the insoluble material was filtered off through celite. The filtrate was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (316.2 mg).

Workup

  1. filtrationthe insoluble material was filtered off through celite
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washthe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3ce17d99bce74870a2e2c908aa03a695
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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