Benzyl Bromide → 1-Benzyl-6-bromo-1H-indole-3-carbaldehyde

HRID 337612

Reaktionsgleichung

Reaktionsgleichung von HRID 337612
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C>[CH2:15]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:10]=2)[C:6]([CH:11]=[O:12])=[CH:7]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 27948306-Bromoindole-3-carbaldehyde

Produkt 1

HCID 866516751-Benzyl-6-bromo-1H-indole-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Bromo-1H-indole-3-carbaldehyde (1 eq.) from the previous step was dissolved in DMF (0.19 M). Sodium hydride was added (1.5 eq.) and the resulting solution was stirred at RT for 20 min. Benzyl bromide (1 eq.) was then added and the reaction solution was allowed to stir at RT for 24 h. The reaction mixture was subsequently quenched with water and extracted with EtOAc. The combined organic extracts were dried over MgSO4. Filtration and concentration of the filtrate in vacuo afforded a yellow oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 4:1 (v/v) Hex:EtOAc 3:7 (v/v) Hex:EtOAc) afforded the title compound as a yellow solid.

Aufarbeitung

  1. stirringto stir at RT for 24 h
  2. customThe reaction mixture was subsequently quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationFiltration and concentration of the filtrate in vacuo
  6. customafforded a yellow oil
  7. customPurification of the crude product
  8. customthus obtained by way of flash chromatography (SiO2, 4:1 (v/v) Hex:EtOAc 3:7 (v/v) Hex:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-dc0bbd6d8f4346c5a4e4e1198226eb3d
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889714B2

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