Cesium carbonate → [6-Bromo-1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-[4-(piperidine-1-sulfonyl)-piperazin-1-yl]-methanone

HRID 1786455노트

반응식

HRID 1786455 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([N:13]3[CH2:18][CH2:17][N:16]([S:19]([N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)(=[O:21])=[O:20])[CH2:15][CH2:14]3)=[O:12])[NH:8]2)=[CH:4][C:3]=1[O:28][CH:29]1[CH2:34][CH2:33][N:32]([CH:35]([CH3:37])[CH3:36])[CH2:31][CH2:30]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>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([N:13]3[CH2:14][CH2:15][N:16]([S:19]([N:22]4[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]4)(=[O:21])=[O:20])[CH2:17][CH2:18]3)=[O:12])[N:8]2[CH:49]([CH3:51])[CH3:50])=[CH:4][C:3]=1[O:28][CH:29]1[CH2:30][CH2:31][N:32]([CH:35]([CH3:37])[CH3:36])[CH2:33][CH2:34]1

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 13551Isopropyl methanesulfonateHCID 516892Sodium BicarbonateHCID 68565981[6-Bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-[4-(piperidine-1-sulfonyl)-piperazin-1-yl]-methanone

생성물 1

HCID 68565698[6-Bromo-1-isopropyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-[4-(piperidine-1-sulfonyl)-piperazin-1-yl]-methanone수율 56%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 100 mg (0.17 mmol) [6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-[4-(piperidine-1-sulfonyl)-piperazin-1-yl]-methanone (example 1) in 3 mL acetonitrile were added 109 mg (0.33 mmol) cesium carbonate and 46 mg (0.33 mmol) isopropyl methanesulfonate. The reaction was stirred under reflux for 18 h. After cooling to room temperature, the reaction mixture was poured into 10% aqueous sodium bicarbonate solution; the phases were separated and 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 residue was purified by flash chromatography on silica gel with a gradient of dichloromethane:methanol (100:0 to 50:50) as eluant, to afford 60 mg (56%) of the product as a light-yellow oil.

후처리

  1. temperatureunder reflux for 18 h
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash chromatography on silica gel with a gradient of dichloromethane:methanol (100:0 to 50:50) as eluant

출처 및 근거

ORD 기록
ord-30cf47e103e547e6aad1f0f986f90b5c
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07507736B2

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