Sodium hydride → 2-(6,7-Dimethoxy-quinoxalin-2-yl)-2-aza-bicyclo[2.2.2]octan-3-one

HRID 23350

Reaktionsgleichung

Reaktionsgleichung von HRID 23350
[CH:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:9])[NH:2]2.[H-].[Na+].Cl[C:13]1[CH:22]=[N:21][C:20]2[C:15](=[CH:16][C:17]([O:25][CH3:26])=[C:18]([O:23][CH3:24])[CH:19]=2)[N:14]=1>C1COCC1.CN(C=O)C>[CH3:24][O:23][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][C:17]=1[O:25][CH3:26])[N:14]=[C:13]([N:2]1[C:3](=[O:9])[CH:4]3[CH2:7][CH2:8][CH:1]1[CH2:6][CH2:5]3)[CH:22]=[N:21]2

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 1378872-Azabicyclo(2.2.2)octan-3-oneHCID 225731372-Chloro-6,7-dimethoxyquinoxaline

Produkt 1

HCID 225731612-(6,7-Dimethoxy-quinoxalin-2-yl)-2-aza-bicyclo[2.2.2]octan-3-oneAusbeute 34,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-Azabicyclo[2.2.2]octan-3-one (228 mg, 2.3 mmole) is dissolved in a mixture of THF/DMF (5 mL/3 mL) and treated with NaH (60%, 184 mg, 4.6 mmole). The resulting mixture is heated at 60° C. for 0.5 hour before addition of 2-chloro-6,7-dimethoxyquinoxaline (344 mg, 1.5 mmole). After being heated at 80° C. overnight, the reaction mixture is concentrated. The residue is chromatographed on silica gel (50% ethyl acetate/hexane) to give 164 mg (23%) of a yellow solid (m.p. 158-159° C.).

Aufarbeitung

  1. concentrationthe reaction mixture is concentrated
  2. customThe residue is chromatographed on silica gel (50% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d4f26f37fe4d4f7f8fb7cf472b32084d
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852712B2

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