Reaction #43328

Reaction equation

4-Fluorostyrene

potassium carbonate

DMF

4-iodo-2-(4-methoxybenzyloxy)pyridine

→

title compound

Yield 61.0%

4-[(E)-2-(4-fluorophenyl)vinyl]-2-(4-methoxybenzyloxy)-pyridine

Yield 61.0%

Solvents

brine

Conditions

Workup

1. 1
   Extractionfollowed by extraction with ethyl acetate
2. 2
   Dryingdrying over anhydrous magnesium sulfate
3. 3
   ConcentrationConcentrating the solvent under reduced pressure
4. 4
   Otherthe resulting residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:19-1:9-1:4)

Procedure

4-Fluorostyrene (3.0 mL), dichlorobis(triphenylphosphine)palladium (870 mg) and potassium carbonate (5.2 g) were added to DMF (70 mL) solution of 4-iodo-2-(4-methoxybenzyloxy)pyridine (4.25 g) 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 resulting residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:19-1:9-1:4) to provide the title compound (2.55 g, 61%).

Source