Diethylaluminum chloride → 2-(6-Methylpyridin-2-yl)-1-(quinoxalin-6-yl)ethan-1-one

HRID 1071574

Reaktionsgleichung

[N:1]1[C:6]([CH3:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].[Li]CCCC.CCCCCC.[Al](Cl)(CC)CC.[N:26]1[C:35]2[C:30](=[CH:31][C:32]([C:36](Cl)=[O:37])=[CH:33][CH:34]=2)[N:29]=[CH:28][CH:27]=1>C1COCC1>[CH3:7][C:6]1[N:1]=[C:2]([CH2:8][C:36]([C:32]2[CH:31]=[C:30]3[C:35](=[CH:34][CH:33]=2)[N:26]=[CH:27][CH:28]=[N:29]3)=[O:37])[CH:3]=[CH:4][CH:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

A stirred solution of 2,6-lutidine (1.4 g, 13 mmole) in dry THF (100 ml) at −60° C. under Ar was treated dropwise with a solution of BuLi in hexane (2.5 M, 5.2 ml, 13 mmole). After 30 mins a solution of Et2AlCl in hexane (14 ml, 14 mmole) was added dropwise and the solution warmed to 20° C. After a further 30 mins the solution was cooled to −50° C. and transferred via canula to a stirred solution of quinoxaline-6-carbonyl chloride (2.0 g, 10.3 mmole) in THF (100 ml) at −60° C. Stirring was continued for 20 min and the solution quenched with sat. aq. NH4Cl solution and warmed to 20° C. The mixture was filtered through Kieselguhr and the filtrate worked up as normal (EtOAc, water, Na2SO4). Filtration through silica eluting with EtOAc gave the product as a yellow solid (1.65 g, 51%). m/z [ESMS]: 264 [M+H]+.

Aufarbeitung

temperatureAfter a further 30 mins the solution was cooled to −50° C.
customthe solution quenched with sat. aq. NH4Cl solution
temperaturewarmed to 20° C
filtrationThe mixture was filtered through Kieselguhr
filtrationFiltration through silica eluting with EtOAc

Quellen und Nachweise

ORD-Eintrag: ord-0e47f117d90f470e9175b38f4ebf4cb3
Quelldatensatz: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06906089B2

Verknüpfte Notizen

Wird geladen…