Benzenesulfonyl chloride → 5-Chloro-1-(phenylsulfonyl)indole

HRID 1677829Notes

Reaction equation

HRID 1677829 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[H-].[Na+].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:13]1([S:19]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 871105-ChloroindoleHCID 516892Sodium Bicarbonate

Product 1

HCID 64726505-Chloro-1-(phenylsulfonyl)indoleYield 77.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-chloroindole (20 g, 131.93 mmol, 1 eq.) in dry DMF (250 mL) at 0° C., was added NaH (5.38 g, 134.57 mmol, 1.02 eq.). After stirring at room temperature for 1 h, benzenesulfonyl chloride (23.77 g, 134.57 mmol, 1.02 eq.) was added slowly. The reaction mixture was stirred for additional 1 h, then poured into 1 L of 5% aq. NaHCO3 and extracted with EtOAc (×3). The organic layers were combined, washed with H2O (×3), brine (×3), dried over (Na2SO4), filtered, and the filtrate was concentrated. The material was purified by flash chromatography to yield 30 g of 1-phenylsulfonyl-5-chloroindole as colorless crystals.

Workup

  1. stirringThe reaction mixture was stirred for additional 1 h
  2. extractionextracted with EtOAc (×3)
  3. washwashed with H2O (×3), brine (×3)
  4. dry with materialdried over (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe material was purified by flash chromatography

Sources & evidence

ORD record
ord-a597ec2baf254bfca9e7c874faa76e8d
Source dataset
uspto-grants-2011_08
Patent number
US08008335B2

Reaction notes

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