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

HRID 1992474

Reaction equation

HRID 1992474 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-4d7750247d5b4b7ea20b23d2787e9dd9
Source dataset
uspto-grants-2010_01
Patent number
US07648979B2

Linked notes

Loading…