N,N'-Dimethylethylenediamine → 1-(4-Bromo-phenyl)-3-isopropyl-1H-pyrazole

HRID 625699노트

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HRID 625699 반응식
[CH:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([CH3:3])[CH3:2].[Br:9][C:10]1[CH:15]=[CH:14][C:13](I)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CNCCNC>CN(C)C=O.[Cu]I.O>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([N:6]2[CH:7]=[CH:8][C:4]([CH:1]([CH3:3])[CH3:2])=[N:5]2)=[CH:12][CH:11]=1

참가 물질

8

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 115221-Bromo-4-iodobenzeneHCID 178439403HCID 178439403, 화합물

생성물 1

HCID 898261621-(4-Bromo-phenyl)-3-isopropyl-1H-pyrazole수율 95.2%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

3-Isopropylpyrazole (588 mg, 5.43 mmol), 1-bromo-4-iodobenzene (15.11 g, 53.4 mmol), cesium carbonate (5.22 g, 16.0 mmol), copper(I)iodide (1.02 g, 5.34 mmol) and N,N′-dimethylethylenediamine (570 uL, 5.34 mmol) are combined in dry N,N-dimethylformamide (100 mL) and heated at 100° C. for 3 hours under a nitrogen atmosphere. The mixture is cooled, poured into water and extracted with diethyl ether. The organic phase is dried and the solvent removed. The residue is purified by flash chromatography (30% dichloromethane in cyclohexane) to give the title compound (Yield 1.37 g) LC (METHOD 5): tR=1.47 min; Mass spectrum (ES+): m/z=265/267 [M+H]+.

후처리

  1. temperatureThe mixture is cooled
  2. extractionextracted with diethyl ether
  3. customThe organic phase is dried
  4. customthe solvent removed
  5. customThe residue is purified by flash chromatography (30% dichloromethane in cyclohexane)

출처 및 근거

ORD 기록
ord-e30691173bd447abb0e7a5745adab4e3
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09308194B2

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