Dimethylformamide → Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-1H-indol-5-yloxy]-butyl}-methyl-amine

HRID 1633706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633706
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[F:16])[N:12]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH:11]=[CH:10]2.[CH2:24]([CH2:27][NH2:28])[CH:25]=C.[OH-].[Na+].[CH3:31]N(C=O)C>>[CH2:27]([N:28]([CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[F:16])[N:12]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH:11]=[CH:10]2)[CH3:31])[CH:24]=[CH2:25]

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 4437323-Buten-1-amineHCID 186794855-(4-Bromo-butoxy)-1-(4-chloro-phenyl)-6-fluoro-1H-indole

Produkt 1

HCID 18679530Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-1H-indol-5-yloxy]-butyl}-methyl-amineAusbeute 85 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

30 mg (0.076 mmol) 5-(4-Bromo-butoxy)-1-(4-chloro-phenyl)-6-fluoro-1H-indole in 0.25 ml DMF were treated with 75 μl of N-Allylmethylamine and stirred at 80° C. during 1 h. The mixture was treated with 0.5M aqueous NaOH and extracted three times with Et2O. Drying of the combined organic layers with Na2SO4, evaporation of the solvent and column chromatography on silica gel with hexane/EtOAc 1:1 gave 25 mg (85%) Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-1H-indol-5-yloxy]-butyl}-methyl-amine as a light yellow oil, MS: 387 (MH+, 1Cl).

Aufarbeitung

  1. extractionextracted three times with Et2O
  2. dry with materialDrying of the combined organic layers with Na2SO4, evaporation of the solvent and column chromatography on silica gel with hexane/EtOAc 1:1

Quellen und Nachweise

ORD-Eintrag
ord-d9649af933174d8c815aa61f0a24261e
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503907B2

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