Sodium hydride → 6-Bromo-1-(4-dimethylsulfamoyl-benzyl)-2-oxo-1,2-dihydro-indole-3,3-dicarboxylic acid di-tert-butyl ester

HRID 1355658Notes

Reaction equation

HRID 1355658 reaction equation
[C:1]([O:5][C:6]([C:8]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:16]2[C:11](=[CH:12][C:13]([Br:17])=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([S:36]([N:39]([CH3:41])[CH3:40])(=[O:38])=[O:37])=[CH:32][CH:31]=1>CN(C)C=O>[C:1]([O:5][C:6]([C:8]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:16]2[C:11](=[CH:12][C:13]([Br:17])=[CH:14][CH:15]=2)[N:10]([CH2:29][C:30]2[CH:31]=[CH:32][C:33]([S:36](=[O:38])(=[O:37])[N:39]([CH3:40])[CH3:41])=[CH:34][CH:35]=2)[C:9]1=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 110440824-(Bromomethyl)-N,N-dimethylbenzenesulfonamideHCID 700343386-Bromo-2-oxo-1,2-dihydro-indole-3,3-dicarboxylic acid di-tert-butyl ester

Product 1

HCID 700321706-Bromo-1-(4-dimethylsulfamoyl-benzyl)-2-oxo-1,2-dihydro-indole-3,3-dicarboxylic acid di-tert-butyl esterYield 114.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Bromo-2-oxo-1,2-dihydro-indole-3,3-dicarboxylic acid di-tert-butyl ester (5.10 g, 12.4 mmol) was dissolved in 40 ml of anhydrous N,N-dimethylformamide (DMF) under an atmosphere of dry N2. The solution was cooled to 0° C. after which time 60% sodium hydride in oil (500 mg, 12.4 mmol) was added and the solution was then stirred for 15 minutes at this temperature. The reaction mixture was the warmed to ambient temperature and stirred for 15 minutes after which time 4-bromomethyl-N,N-dimethyl-benzenesulfonamide (3.44 g, 12.4 mmol) was added. The mixture was stirred overnight after which time it was concentrated under vacuum and partitioned between DCM and water. The DCM layer was washed 3 more times with water, once with brine, dried over MgSO4, filtered and concentrated under vacuum to give 8.63 g of the titled compound as a yellow solid

Workup

  1. additionwas added
  2. additionwas added
  3. stirringThe mixture was stirred overnight after which time it
  4. concentrationwas concentrated under vacuum
  5. custompartitioned between DCM and water
  6. washThe DCM layer was washed 3 more times with water
  7. dry with materialonce with brine, dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1e2bd8fd3cdd4f49bff0f5aae27a6315
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

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