Benzenesulfonyl chloride → ethyl 5-chloro-1-(phenylsulfonyl)-1H-indole-2-carboxylate

HRID 227463노트

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HRID 227463 반응식
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>CCCCCC.CN(C=O)C.CCOC(C)=O>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([S:24]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:26])=[O:25])[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2

참가 물질

8

반응물 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 78518Ethyl 5-chloroindole-2-carboxylateHCID 516892Sodium Bicarbonate

생성물 1

HCID 22401489ethyl 5-chloro-1-(phenylsulfonyl)-1H-indole-2-carboxylate

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

A 60% dispersion of NaH in mineral oil (1.07 g, 26.9 mmol) was washed with hexane, and the resulting powder was suspended in 40 mL of DMF. After cooling the stirred mixture to 0° C., ethyl 5-chloro-1H-indole-2-carboxylate (5.00 g, 22.4 mmol) was added in portions. The solution was warmed to room temperature, during which gas was released. After 15 minutes, the mixture was cooled again to 0° C., and benzenesulfonyl chloride was added dropwise (3.14 mL, 24.6 mmol). After warming to room temperature, the reaction was stirred for 1.5 hours, then poured into a mixture of EtOAc and saturated aqueous NaHCO3 solution. The organic phase was washed with water and brine, dried with Na2SO4, filtered, and concentrated in vacuo. The resulting solid was stirred in 50 mL of a 10% EtOAc/hexane solution for 30 minutes, then filtered to provide the titled product as a white powder. Proton NMR for the product was consistent with the titled compound. ESI+MS: 364.1 [M+H]+.

후처리

  1. temperatureThe solution was warmed to room temperature, during which gas
  2. temperaturethe mixture was cooled again to 0° C.
  3. temperatureAfter warming to room temperature
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. stirringThe resulting solid was stirred in 50 mL of a 10% EtOAc/hexane solution for 30 minutes
  9. filtrationfiltered

출처 및 근거

ORD 기록
ord-1bf170119bc047e0a29d351add28608f
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560546B2

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