Benzenesulfonyl chloride → 1-benzenesulfonyl-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine

HRID 1515902Notes

Reaction equation

HRID 1515902 reaction equation
[CH2:1]([S:3][C:4]1[CH:5]=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1)[CH3:2].[OH-].[Na+].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[C:15]1([S:21]([N:10]2[C:7]3=[N:8][CH:9]=[C:4]([S:3][CH2:1][CH3:2])[CH:5]=[C:6]3[CH:12]=[CH:11]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 672279375-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 672294751-benzenesulfonyl-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridineYield 63%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine (2.7 g, 15.2 mmol), sodium hydroxide (1.82 g, 45.6 mmol) and tetrabutylammonium bromide (150 mg, 0.46 mmol) in dichloromethane (30 mL) at 0° C. was added benzenesulfonyl chloride (4.0 g, 22.8 mmol) dropwise. After stirring for 12 h at room temperature, the mixture was washed with water (2×10 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 50% dichloromethane/hexanes) to afford 1-benzenesulfonyl-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridine (2.68 g, 63%): LC/MS m/e calcd for C15H14N2O2S2 [M+H]+ 319.42, observed 319.1.

Workup

  1. washthe mixture was washed with water (2×10 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 50% dichloromethane/hexanes)

Sources & evidence

ORD record
ord-62ec7fcb74f7450ba74549543f011a30
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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