6-Bromo-1-(4-dimethylsulfamoyl-benzyl)-2-oxo-1,2-dihydro-indole-3,3-dicarboxylic acid di-tert-butyl ester → 4-(6-Bromo-2-oxo-2,3-dihydro-indol-1-ylmethyl)-n,n-dimethyl-benzenesulfonamide

HRID 1355659Notes

Reaction equation

HRID 1355659 reaction equation
C(OC([C:8]1(C(OC(C)(C)C)=O)[C:16]2[C:11](=[CH:12][C:13]([Br:17])=[CH:14][CH:15]=2)[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([S:25](=[O:30])(=[O:29])[N:26]([CH3:28])[CH3:27])=[CH:21][CH:20]=2)[C:9]1=[O:31])=O)(C)(C)C>FC(F)(F)C(O)=O>[Br:17][C:13]1[CH:12]=[C:11]2[C:16]([CH2:8][C:9](=[O:31])[N:10]2[CH2:18][C:19]2[CH:20]=[CH:21][C:22]([S:25]([N:26]([CH3:27])[CH3:28])(=[O:30])=[O:29])=[CH:23][CH:24]=2)=[CH:15][CH:14]=1

Participants

3

Reactant 1

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

Product 1

HCID 185077814-(6-Bromo-2-oxo-2,3-dihydro-indol-1-ylmethyl)-n,n-dimethyl-benzenesulfonamideYield 90.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

6-Bromo-1-(4-dimethylsulfamoyl-benzyl)-2-oxo-1,2-dihydro-indole-3,3-dicarboxylic acid di-tert-butyl ester (10.0 g, 16.4 mmol) was dissolved in 50 ml of trifluoroacetic acid (TFA) under an atmosphere of dry N2 and stirred overnight at ambient temperature. The reaction mixture was then concentrated under vacuum and partitioned between DCM and saturated aqueous sodium bicarbonate (NaHCO3). The DCM layer was then dried over MgSO4, filtered and concentrated under vacuum to give 6.05 g of the titled compound as a white solid.

Workup

  1. concentrationThe reaction mixture was then concentrated under vacuum
  2. custompartitioned between DCM and saturated aqueous sodium bicarbonate (NaHCO3)
  3. dry with materialThe DCM layer was then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-de43736401324176ab63ee47d4daa473
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

Loading…