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

HRID 625699ノート

反応式

HRID 625699 の反応式
[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

参加物

8

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 115221-Bromo-4-iodobenzeneHCID 178439403HCID 178439403、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-e30691173bd447abb0e7a5745adab4e3
出典データセット
uspto-grants-2016_04
特許番号
US09308194B2

反応ノート

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