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

HRID 227463ノート

反応式

HRID 227463 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-1bf170119bc047e0a29d351add28608f
出典データセット
uspto-grants-2009_07
特許番号
US07560546B2

反応ノート

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