Potassium Carbonate → 2-Methyl-1'-[4-(trifluoromethyl)phenyl]-1'H,2H-3,4'-bipyrazole

HRID 238371ノート

反応式

HRID 238371 の反応式
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[N:9][NH:10][CH:11]=2)=[CH:5][CH:4]=[N:3]1.I[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC.[Cl-].[NH4+]>[Cu](I)I.CN(C)C=O>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[N:9][N:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH:11]=2)=[CH:5][CH:4]=[N:3]1

参加物

8

反応物 5

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 1363877762-Methyl-1'H,2H-3,4'-bipyrazole

生成物 1

HCID 895587402-Methyl-1'-[4-(trifluoromethyl)phenyl]-1'H,2H-3,4'-bipyrazole収率 80.7%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Under a nitrogen atmosphere, a mixture of 2-methyl-1′H,2H-3,4′-bipyrazole (176 mg), 4-iodobenzotrifluoride (485 mg), copper iodide (45 mg), potassium carbonate (329 mg), trans-N,N′-dimethylcyclohexan-1,2-diamine (135 mg) and N,N-dimethylformamide (2.2 mL) was stirred at 100° C. for 16 hours. Thereafter, a saturated ammonium chloride aqueous solution was added to the reaction solution, and the obtained mixture was then extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and was then concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1 to 1:1), so as to obtain the title compound (280 mg) in the form of a colorless solid.

後処理

  1. extractionthe obtained mixture was then extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationwas then concentrated under a reduced pressure
  4. customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1 to 1:1)

出典と根拠

ORDレコード
ord-325bb98fb8fd415ea261e8d718bd0fed
出典データセット
uspto-grants-2014_02
特許番号
US08642626B2

反応ノート

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