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

HRID 1159781Notes

Reaction equation

HRID 1159781 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-e6b77c22118a43229d702192b50cc658
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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