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

Participants

Reaction Conditions

Reaction Steps

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]+.

Provenance & Evidence