Benzenesulfonyl chloride → HCID 67229432, compound

HRID 1515869Notes

Reaction equation

HRID 1515869 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[NH:9][CH:10]=[CH:11][C:6]2=[CH:5][CH:4]=1.[OH-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[C:14]1([S:20]([N:9]2[C:7]3=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=[C:6]3[CH:11]=[CH:10]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 116151916-Methoxy-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 67229432HCID 67229432, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-methoxy-1H-pyrrolo[2,3-b]pyridine (1.2 g, 8.1 mmol), sodium hydroxide (0.97 g, 24.3 mmol) and tetrabutylammonium bromide (78.4 mg, 0.24 mmol) in dichloromethane (50 mL) at 0° C. was added benzenesulfonyl chloride (2.14 g, 12.15 mmol) dropwise. The resulting mixture was stirred for 12 h at room temperature. The mixture was washed with water (2×10 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue which was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 100% dichloromethane) to afford 1-benzenesulfonyl-6-methoxy-1H-pyrrolo[2,3-b]pyridine (2.0 g, 85%): LC/MS m/e calcd for C14H12N2O3S [M+H]+ 290.33, observed 289.0.

Workup

  1. washThe mixture was washed with water (2×10 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give a residue which
  5. customwas purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 100% dichloromethane)

Sources & evidence

ORD record
ord-ce34f3fabfcc4d278359ccd3ed92ab0b
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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