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

HRID 1669688

Reaktionsgleichung

Reaktionsgleichung von HRID 1669688
[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]

Komponenten

5

Edukt 4

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

Produkt 1

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

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-169acb8f58614fcdab9af4de2434f843
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989624B2

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