Benzenesulfonyl chloride → 4-Bromo-6-methoxy-1-(phenylsulfonyl)-1H-indole

HRID 1159781ノート

反応式

HRID 1159781 の反応式
[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20]

参加物

6

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 247280264-bromo-6-methoxy-1H-indole2 回

生成物 1

HCID 687186244-Bromo-6-methoxy-1-(phenylsulfonyl)-1H-indole

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 6344Dichloromethane溶媒

実験手順

4-Bromo-6-methoxy indole (0.07 g, 0.3 mmol) was dissolved in dry dichloromethane (4 mL) and benzenesulphonyl chloride (0.06 g, 0.3 mmol), tetrabutylammonium hydrogen sulphate (0.01 g, 0.01 mmol) and 4N NaOH (0.5 mL) were added and the mixture was stirred at rt for 50 min. The mixture was extracted with water (2×4 mL), dried (Na2SO4) and evaporated. The crude product was combined with an earlier batch of this intermediate (followed this experimental and starting with 4-bromo-6-methoxy indole (0.35 g, 1.5 mmol). MS (ESI+) for C15H12BrNO3S m/z 366 (M+H)+.

後処理

  1. extractionThe mixture was extracted with water (2×4 mL)
  2. dry with materialdried (Na2SO4)
  3. customevaporated

出典と根拠

ORDレコード
ord-e6b77c22118a43229d702192b50cc658
出典データセット
uspto-grants-2010_10
特許番号
US07812017B2

反応ノート

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