Allyl bromide → HCID 67344093, Verbindung

HRID 1518250Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1518250
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[CH2:28][O:29][Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:42](Br)[CH:43]=[CH2:44]>CN(C=O)C>[CH2:44]([N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:11]=2)[C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:8]1[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[CH2:28][O:29][Si:30]([CH:31]([CH3:32])[CH3:33])([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])[CH:43]=[CH2:42]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 67345419methyl 3-cyclohexyl-2-(4-methoxy-2-{[(triisopropylsilyl)oxy]methyl}phenyl)-1H-indole-6-carboxylate

Produkt 1

HCID 67344093HCID 67344093, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl 3-cyclohexyl-2-(4-methoxy-2-{[(triisopropylsilyl)oxy]methyl}phenyl)-1H-indole-6-carboxylate (1 eq.) was dissolved in DMF (0.34M solution) and the solution was degassed. NaH (1.1 eq.) was added and the mixture was left stirring for 5 min. Allyl bromide (1.2 eq.) was added and stirring was continued for 5 h. All volatiles were evaporated in vacuo and the residual material was dissolved in Et2O. The solution was washed with 0.5N HCl, saturated aq. NaHCO3 solution and with brine. After drying the organic phase over Na2SO4 all volatiles were evaporated in vacuo and the residual material was purified by flash chromatography (PE:EtOAc, 10:1). After evaporation of the solvents the product was obtained as a colorless sticky solid (84%). The material was used without further characterization in the next reaction.

Aufarbeitung

  1. customthe solution was degassed
  2. waitthe mixture was left
  3. stirringstirring
  4. waitwas continued for 5 h
  5. customAll volatiles were evaporated in vacuo
  6. dissolutionthe residual material was dissolved in Et2O
  7. washThe solution was washed with 0.5N HCl, saturated aq. NaHCO3 solution and with brine
  8. dry with materialAfter drying the organic phase over Na2SO4 all volatiles
  9. customwere evaporated in vacuo
  10. customthe residual material was purified by flash chromatography (PE:EtOAc, 10:1)
  11. customAfter evaporation of the solvents the product

Quellen und Nachweise

ORD-Eintrag
ord-e3d0c435ada94809b12be6f2808e1849
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232390B2

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