Potassium Carbonate → 4-(6-Bromo-7-methyl-2,3-dioxo-2,3-dihydro-indol-1-ylmethyl)-n,n-dimethyl-benzenesulfonamide

HRID 1355675Notes

Reaction equation

HRID 1355675 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([C:6](=[O:13])[C:7](=[O:12])[NH:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:31]([CH3:33])[CH3:32])(=[O:30])=[O:29])=[CH:24][CH:23]=1>CN(C=O)C>[Br:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([C:6](=[O:13])[C:7](=[O:12])[N:8]2[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([S:28]([N:31]([CH3:32])[CH3:33])(=[O:30])=[O:29])=[CH:24][CH:23]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 110440824-(Bromomethyl)-N,N-dimethylbenzenesulfonamideHCID 112301886-Bromo-7-methyl-1H-indole-2,3-dione

Product 1

HCID 185077734-(6-Bromo-7-methyl-2,3-dioxo-2,3-dihydro-indol-1-ylmethyl)-n,n-dimethyl-benzenesulfonamideYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-7-methyl-1H-indole-2,3-dione (2.0 g, 8.33 mmol) in DMF (25 ml) was added potassium carbonate (2.3 g, 16.6 mmol). After stirring at this temperature for 30 minutes, was added 4-bromomethyl-N,N-dimethyl-benzenesulfonamide (3.0 g, 10.83 mmol). The reaction mixture was stirred at room temperature for six hours. It was then partitioned between water and ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated under vacuum to give the crude product which was chromatographed on flash silica gel eluting with 20% ethyl acetate in hexane, providing the title compound of 12A (0.392 g, 11% yield).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for six hours
  2. customIt was then partitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give the crude product which
  7. customwas chromatographed on flash silica gel eluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1df5de893e8547e7b63c7c26edafaa0b
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

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