Reacción #2123085

Ecuación de reacción

picolinic acid

4-(2-aminopyridin-3-yl)phenol

tripotassium phosphate

1-bromo-3-(1,1-difluoroethyl)benzene

→

title compound

Rendimiento 56.9%

3-(4-(3-(1,1-difluoroethyl)phenoxy)phenyl)pyridin-2-amine

Rendimiento 56.9%

Disolventes

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONActivated carbon was added
2. 2
   Otrothe insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc)
3. 3
   workup.ADDITIONSilica-gel was added to the filtrate
4. 4
   Otrothe volatiles were removed in vacuo
5. 5
   Otrowas purified by column chromatography (NH-silica gel, eluted with EtOAc in hexane)
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

Procedimiento

Copper(I) iodide (102 mg) was added to a mixture of picolinic acid (66.1 mg), 4-(2-aminopyridin-3-yl)phenol (500 mg), tripotassium phosphate (1710 mg), 1-bromo-3-(1,1-difluoroethyl)benzene (712 mg) and DMSO (8 mL). The mixture was stirred at 130° C. under nitrogen for 10 hr. Activated carbon was added and the insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc). Silica-gel was added to the filtrate and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH-silica gel, eluted with EtOAc in hexane) and concentrated. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (499 mg) as pale yellow oil.

Fuente