Reaktion #41944

Reaktionsgleichung

6-Bromo-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinoline

compound

6-Bromo-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinoline

cyclopropyboronic acid

potassium phosphate tribasic

→

white crystals

Ausbeute 22.2%

6-Cyclopropyl-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinoline

Ausbeute 22.2%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturat reflux under argon for 8 h
3. 3
   ExtraktionAfter extraction with dichloromethane and half-saturated NaCl solution
4. 4
   Sonstigethe crude product was purified chromatography on silica gel in dichloromethane/ethyl acetate with a gradient from 100:0 to 90:10

Vorschrift

6-Bromo-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinoline (compound of example 6) (0.5 g, 1.3 mmol), cyclopropyboronic acid (0.167 g, 1.95 mmol), potassium phosphate tribasic (0.826 g, 3.89 mmol) and tetrakis(triphenylphosphine)palladium(0) (45 mg, 0.039) were mixed together in dioxane (7 mL) and heated at reflux under argon for 8 h. After extraction with dichloromethane and half-saturated NaCl solution, the crude product was purified chromatography on silica gel in dichloromethane/ethyl acetate with a gradient from 100:0 to 90:10. One obtained 0.1 g (21%) of white crystals. MS: m/z=347 (M+H).

Quelle