Reaktion #41935

Reaktionsgleichung

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

cesium carbonate

morpholine

→

solid

Ausbeute 78.6%

3-Methanesulfonyl-2-methyl-6-morpholin-4-yl-4-phenyl-quinoline

Ausbeute 78.6%

Lösungsmittel

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 80:20

Vorschrift

A tube placed under argon was charged with tris(dibenzylideneacetone)dipalladium chloroform complex (55 mg, 0.053 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (63 mg, 0.106 mmol) and cesium carbonate (1.3 g, 3.99 mmol). 6-Bromo-3-methanesulfonyl-2-methyl-4-phenyl-quinoline (compound of example 2) (1 g, 2.66 mmol) in tert.-butanol (20 ml) was added, followed by morpholine (0.28 g, 3.19 mmol). The tube was sealed and heated at 110° 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 80:20 to give a yellow solid (800 mg, 78%). MS: m/z=383 (M+H).

Quelle