Reaktion #41949

Reaktionsgleichung

morpholine

2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl

cesium carbonate

6-Bromo-3-methanesulfonyl-2-methyl-4-(4-trifluoromethyl-phenyl)-quinoline

→

solid

Ausbeute 36.4%

3-Methanesulfonyl-2-methyl-6-morpholin-4-yl-4-(4-trifluoromethyl-phenyl)-quinoline

Ausbeute 36.4%

Lösungsmittel

heptane

tert.-butanol

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 with a gradient 100:0 to 40:60

Vorschrift

A tube placed under argon was charged with tris(dibenzylideneacetone)dipalladium chloroform complex (51 mg, 0.05 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (47 mg, 0.10 mmol) and cesium carbonate (1.21 g, 3.71 mmol). 6-Bromo-3-methanesulfonyl-2-methyl-4-(4-trifluoromethyl-phenyl)-quinoline (compound of example 20) (800 mg, 1.95 mmol) in tert.-butanol (20 ml) was added, followed by morpholine (0.259 g, 2.97 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 with a gradient 100:0 to 40:60 to give a yellow solid (320 mg, 29%). MS: m/z=451 (M+H).

Quelle