Dimethylformamide → 7-Bromo-1,3,3-trimethylindolin-2-one

HRID 1097436

Reaction equation

HRID 1097436 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2C=1N[C:8](=O)[CH2:7]2.[C:12](=O)([O-])[O-].[Cs+].[Cs+].IC.[CH3:20][N:21]([CH:23]=[O:24])[CH3:22]>>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:20]=1[N:21]([CH3:22])[C:23](=[O:24])[C:7]2([CH3:8])[CH3:12]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 27732917-bromo-2,3-dihydro-1H-indol-2-one

Product 1

HCID 668128797-Bromo-1,3,3-trimethylindolin-2-one

Procedure

To a solution of 7-bromo-1,3-dihydro-2H-indol-2-one (200 mg, 0.94 mmol) in DMF (5 mL) were added cesium carbonate (676 mg, 2.07 mmol) and iodomethane (294 mg, 2.07 mmol). The reaction mixture was stirred at ambient temperature for 18 h, then partitioned between H2O (50 mL) and EtOAc (100 mL). The organic extract was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 85:15, to give the title compound. MS: m/z=254 (M+1).

Workup

  1. custompartitioned between H2O (50 mL) and EtOAc (100 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-c9c08a7524874cc8bcde04a58e7c999f
Source dataset
uspto-grants-2012_03
Patent number
US08143266B2

Linked notes

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