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

HRID 1159781노트

반응식

HRID 1159781 반응식
[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]

참가 물질

6

반응물 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 247280264-bromo-6-methoxy-1H-indole2회

생성물 1

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

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-e6b77c22118a43229d702192b50cc658
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812017B2

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