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

HRID 70251

Reaktionsgleichung

Reaktionsgleichung von HRID 70251
[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]

Komponenten

9

Edukt 3

HCID 11430Potassium CarbonateHCID 67868Benzene, 1-iodo-3-(trifluoromethyl)-HCID 178423828HCID 178423828, Verbindung2×

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 438061,2-Diaminocyclohexane, trans-KatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7ffe904866334572985715c6e26116d9
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822521B2

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