Sodium hydride → HCID 18007495, compound

HRID 988095Notes

Reaction equation

HRID 988095 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[S:14]([CH3:13])(=[O:16])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 6764936-Bromoindole

Product 1

HCID 18007495HCID 18007495, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-Bromoindole (1.82 g, 9 mmol) in DMF at 0° C. was added NaH (446 mg, 18 mmol). The mixture was allowed to warm to room temperature and stirred for 15 min. The reaction was then cooled to 0° C., MeSO2Cl (1.55 g, 13.5 mmol) added and the mixture stirred at this temperature for 1.5 h before being quenched with ice and diluted with ethyl acetate. The organic extract was washed with brine and dried over anhydrous Na2SO4. The crude residue was purified by flash chromatography to give the title product as a white solid (782 mg, 29% yield).

Workup

  1. temperatureThe reaction was then cooled to 0° C.
  2. stirringthe mixture stirred at this temperature for 1.5 h
  3. custombefore being quenched with ice
  4. additiondiluted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7240442e4dcc4b22912f93263084d9ce
Source dataset
uspto-grants-2003_10
Patent number
US06635639B2

Reaction notes

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