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

HRID 70251

反応式

HRID 70251 の反応式
[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]

参加物

9

反応物 3

HCID 11430Potassium CarbonateHCID 67868Benzene, 1-iodo-3-(trifluoromethyl)-HCID 178423828HCID 178423828、化合物2 回

生成物 1

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

試薬・触媒・溶媒 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 438061,2-Diaminocyclohexane, trans-触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7ffe904866334572985715c6e26116d9
出典データセット
uspto-grants-2014_09
特許番号
US08822521B2

関連ノート

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