Reacción #41944

Ecuación de reacción

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

Rendimiento 22.2%

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

Rendimiento 22.2%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente