HCID 15524202, Verbindung → HCID 9821723, Verbindung

HRID 1532623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1532623
[CH2:1]([N:5]1[C:13]2[C:8](=[C:9]([F:14])[CH:10]=[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:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[CH:7]=[CH:6][N:5]2[CH2:1][CH:2]([OH:4])[CH2:3][N:15]1[CH2:16][CH:17]=[C:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:19][CH2:20]1

Komponenten

3

Edukt 2

HCID 15524202HCID 15524202, VerbindungHCID 21184334HCID 21184334, Verbindung

Produkt 1

HCID 9821723HCID 9821723, VerbindungAusbeute 53 %

Versuchsvorschrift

A methanolic solution of 1-N-glycidyl-4-fluoroindole (0.52 g, 3.0 mmole) from example 3 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 pale yellow colored solid (0.61 g, 53% yield). Treatment with a 0.25M ethanolic solution of fumaric acid (0.5 equivalents) gave the required product 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-3ee7ebbc28a848da8b065da5fb0c5f82
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06204274B1

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