Reacción #43334

Ecuación de reacción

9-Borabicyclo[3.3.1]nonane

4-fluorostyrene

compound

4-[(E)-2-(4-Fluorophenyl)vinyl]-1-{4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-1H-pyridin-2-one

sodium carbonate

→

title compound

Rendimiento 100.0%

4-[2-(4-fluorophenyl)ethyl]-2-(4-methoxybenzyloxy)-pyridine

Rendimiento 100.0%

Disolventes

THF

DMF

brine

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTo the reaction liquid
2. 2
   workup.STIRRINGstirred at 100° C. for 19 hours
3. 3
   Extracciónfollowed by extraction with ethyl acetate
4. 4
   Secadodrying over anhydrous magnesium sulfate
5. 5
   ConcentraciónConcentrating the solvent under reduced pressure
6. 6
   Otrothe residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:9-1:4)

Procedimiento

9-Borabicyclo[3.3.1]nonane (540 mg) was added to THF solution (5 mL) of 4-fluorostyrene (240 mL) and stirred at room temperature for 2 hours. To the reaction liquid, the compound synthesized in Step (1) of Example 45(340 mg), tetrakis(triphenylphosphine)palladium (60 mg), DMF (5 mL) and 2M aqueous sodium carbonate solution (1 mL) were added and stirred at 100° C. for 19 hours. Saturated brine was added to the reaction liquid, followed by extraction with ethyl acetate and drying over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:9-1:4) to provide the title compound (336 mg, 100%).

Fuente