Cesium carbonate → (4-Benzenesulfonyl-piperazin-1-yl)-[1-isopropyl-5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone

HRID 1992474

反応式

HRID 1992474 の反応式
[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([C:18]3[NH:19][C:20]4[C:25]([CH:26]=3)=[CH:24][C:23]([C:27]([N:29]3[CH2:34][CH2:33][N:32]([CH:35]([CH3:37])[CH3:36])[CH2:31][CH2:30]3)=[O:28])=[CH:22][CH:21]=4)=[O:17])[CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[CH:49]([CH3:51])[CH3:50])(=O)=O.C(=O)(O)[O-].[Na+]>C(#N)C>[C:1]1([S:7]([N:10]2[CH2:11][CH2:12][N:13]([C:16]([C:18]3[N:19]([CH:49]([CH3:51])[CH3:50])[C:20]4[C:25]([CH:26]=3)=[CH:24][C:23]([C:27]([N:29]3[CH2:30][CH2:31][N:32]([CH:35]([CH3:37])[CH3:36])[CH2:33][CH2:34]3)=[O:28])=[CH:22][CH:21]=4)=[O:17])[CH2:14][CH2:15]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 13551Isopropyl methanesulfonateHCID 516892Sodium BicarbonateHCID 68535846(4-Benzenesulfonyl-piperazin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone

生成物 1

HCID 68536609(4-Benzenesulfonyl-piperazin-1-yl)-[1-isopropyl-5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone収率 39%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A suspension of 0.20 g (0.38 mmol) (4-benzenesulfonyl-piperazin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone (example 13), 0.25 g (0.77 mmol) caesium carbonate and isopropyl methanesulfonate in 4 mL acetonitrile was heated 16 h under reflux. After cooling to room temperature, the mixture was poured into saturated aqueous sodium bicarbonate solution and the phases were separated. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel with dichloromethane:methanol (19:1 v/v) as eluant to afford 0.85 g (39%) of the desired compound as a light brown foam. MS (ISP): 566.4 (M+H)+.

後処理

  1. temperaturewas heated 16 h
  2. temperatureunder reflux
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted three times with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by flash chromatography on silica gel with dichloromethane:methanol (19:1 v/v) as eluant

出典と根拠

ORDレコード
ord-4d7750247d5b4b7ea20b23d2787e9dd9
出典データセット
uspto-grants-2010_01
特許番号
US07648979B2

関連ノート

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