Reaktion #41934

Reaktionsgleichung

6-Bromo-3-methanesulfonyl-2-methyl-4-phenyl-quinoline

cesium carbonate

piperidine

→

solid

3-Methanesulfonyl-2-methyl-4-phenyl-6-piperidin-1-yl-quinoline

Lösungsmittel

dioxane tert.-butanol

heptane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA tube placed under argon
2. 2
   SonstigeThe tube was sealed
3. 3
   TemperaturThe reaction mixture was cooled to 20° C.
4. 4
   Filtrationfiltered through dicalite
5. 5
   Sonstigepurified directly by flash chromatography on silica gel in heptane/ethyl acetate 40:60

Vorschrift

A tube placed under argon was charged with tris(dibenzylideneacetone)dipalladium chloroform complex (3 mg), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (3 mg) and cesium carbonate (121 mg, 0.37 mmol). 6-Bromo-3-methanesulfonyl-2-methyl-4-phenyl-quinoline (compound of example 2) (100 mg, 0.26 mmol) in dioxane/tert.-butanol 1:1 (15 ml) was added, followed by piperidine (0.027 ml, 0.031 mmol). The tube was sealed and heated at 120° C. for 2 h. The reaction mixture was cooled to 20° C., diluted with heptane, filtered through dicalite and purified directly by flash chromatography on silica gel in heptane/ethyl acetate 40:60 to give a yellow solid (47 mg, 46%). MS: m/z=381 (M+H).

Quelle