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

HRID 238371노트

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HRID 238371 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-325bb98fb8fd415ea261e8d718bd0fed
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642626B2

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