5-Fluoro-1-(2-oxiranylmethyl)-1H-indole → HCID 9800520, Verbindung

HRID 1532621Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1532621
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)[CH:2]1[O:4][CH2:3]1.[NH:15]1[CH:20]=[CH:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1>>[F:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:1][CH:2]([OH:4])[CH2:3][N:15]1[CH2:16][CH:17]=[C:18]([C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[NH:23][CH:22]=3)[CH2:19][CH2:20]1)[CH:6]=[CH:7]2

Komponenten

3

Edukt 2

HCID 155242005-Fluoro-1-(2-oxiranylmethyl)-1H-indoleHCID 21184334HCID 21184334, Verbindung

Produkt 1

HCID 9800520HCID 9800520, VerbindungAusbeute 78 %

Versuchsvorschrift

A methanolic solution of 1-N-glycidyl-5-fluoroindole (0.52 g, 3.0 mmole) from example 1 and 3-(4-tetrahydropyridinyl)indole (0.59 g, 3.0 mmole) was refluxed under nitrogen for 15 hours. The reaction mixture was concentrated in vacuo and the product purified by flash silica gel chromatography (ethyl acetate) to afford the titled compound as a light yellow colored solid (0.91 g, 78% yield). Treatment with a 0.25 M ethanolic solution of fumaric acid (0.5 equivalents) gave the required salt as a yellow colored solid. The product was recrystallized from ethanol.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe product purified by flash silica gel chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f2cdf2e8115b4d7ea761f941baf72bc6
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06204274B1

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