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Bromoacetyl bromide → 2-bromo-1-(9H-pyrido[2,3-b]indol-6-yl)ethanone

HRID 341280
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 341280
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:13][C:12]3[N:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:5]=2[CH:6]=1.[Al+3].[Cl-].[Cl-].[Cl-].[Br:18][CH2:19][C:20](Br)=[O:21]>C(Cl)Cl>[Br:18][CH2:19][C:20]([C:1]1[CH:6]=[C:5]2[C:4](=[CH:3][CH:2]=1)[NH:13][C:12]1[N:11]=[CH:10][CH:9]=[CH:8][C:7]2=1)=[O:21]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 61147Bromoacetyl bromideHCID 674869H-Pyrido(2,3-b)indoleHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 585145292-bromo-1-(9H-pyrido[2,3-b]indol-6-yl)ethanoneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 0.2 M stirred suspension of the α-carboline derivative (200 mg) in anhydrous CH2Cl2 was added AlCl3 (4.5 equiv.) and bromoacetyl bromide (2.1 equiv.), at room temperature under inert atmosphere. The mixture was stirred at reflux until completion of the reaction (followed by t.l.c.). The resulting mixture was then cautiously quenched at 0° C. with H2O. It was extracted with the mixture of EtOAc/DMF (99:1). The resulting organic layer was washed with NaHCO3 saturated aqueous solution and brine, dried over MgSO4, filtered and solvents were removed under reduced pressure. 2-Bromo-1-(9H-pyrido[2,3-b]indol-6-yl)ethanone was obtained in 61% yield after trituration of the crude product in MeOH and filtration

Aufarbeitung

  1. customat room temperature
  2. stirringThe mixture was stirred
  3. temperatureat reflux until completion of the reaction (followed by t.l.c.)
  4. customThe resulting mixture was then cautiously quenched at 0° C. with H2O
  5. extractionIt was extracted with the mixture of EtOAc/DMF (99:1)
  6. washThe resulting organic layer was washed with NaHCO3 saturated aqueous solution and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customsolvents were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-162228acfc8042b49d4148281349f85a
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08895744B2

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