Water → HCID 68281577, Verbindung

HRID 2278593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2278593
Cl.C([N+](CCCC)(CCCC)CCCC)CCC.C(N(CC)CC)C.Br[C:27]1[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=1[N:34]([CH2:38][C:39]([CH3:41])=[CH2:40])[C:35](=[O:37])[CH3:36].O>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:33][C:32]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:27]=1[C:39]([CH3:41])([CH3:40])[CH2:38][N:34]2[C:35](=[O:37])[CH3:36]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 18314301HCID 18314301, VerbindungHCID 68281537HCID 68281537, Verbindung

Produkt 1

HCID 68281577HCID 68281577, VerbindungAusbeute 47,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

59 mg of palladium acetate, 1.5 g of tetrabutylammonium hydrochloride and 1.8 ml of triethylamine are added to a solution of 1.5 g of N-(2-bromo-3-fluorophenyl)-N-(2-methylallyl)acetamide in 10 ml of N,N-dimethylformamide. The reaction mixture is heated at 100° C. under an argon atmosphere for 16 hours. After cooling, 50 ml of water are added and the mixture is extracted with ethyl acetate. The organic phase is then washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica column chromatography, elution being carried out with a mixture of heptane and ethyl acetate (50/50: v/v), so as to give 520 mg of 1-(4-fluoro-3,3-dimethyl-2,3-dihydroindol-1-yl)ethanone in the form of a yellow oil.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe organic phase is then washed with water
  4. dry with materiala saturated sodium chloride solution, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica column chromatography, elution
  8. additionbeing carried out with a mixture of heptane and ethyl acetate (50/50: v/v)

Quellen und Nachweise

ORD-Eintrag
ord-60568b451da64059a9f41334e396e03b
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133168B2

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