Reaktion #41946

Reaktionsgleichung

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

cesium carbonate

morpholine

→

solid

4-(4-Fluoro-phenyl)-3-methanesulfonyl-2-methyl-6-morpholin-4-yl-quinoline

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 with a gradient from 100:0 to 40:60

Vorschrift

A tube placed under argon was charged with tris(dibenzylideneacetone)dipalladium chloroform complex (79 mg, 0.076 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (73 mg, 0.152 mmol) and cesium carbonate (1.86 g, 5.7 mmol). 6-Bromo-4-(4-fluoro-phenyl)-3-methanesulfonyl-2-methyl-quinoline (compound of example 14) (200 mg, 0.52 mmol) in tert.-butanol (20 ml) was added, followed by morpholine (0.40 g, 4.56 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 from 100:0 to 40:60 to give a yellow solid (850 mg, 56%). MS: m/z=401 (M+H).

Quelle