Reaction #43333

Reaction equation

Potassium carbonate

methyl p-toluenesulfonate

DMF

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

→

title compound

Yield 53.0%

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

Yield 53.0%

Solvents

Ethyl acetate

Conditions

Workup

1. 1
   Washby washing with water and saturated brine
2. 2
   Dryingdrying over anhydrous sodium sulfate
3. 3
   ConcentrationConcentrating
4. 4
   Otherthe reaction liquid under reduced pressure
5. 5
   Otherthe residue was purified on silica gel column chromatography (C-300; methanol:chloroform=1:20-1:10)

Procedure

Potassium carbonate (11 mg, 0.08 mmol) and methyl p-toluenesulfonate (6 mg, 0.03 mmol) were added to DMF (2 mL) solution of 4-[(E)-2-4-hydroxyphenyl)vinyl]-1-{4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-1H-pyridin-2-one (11 mg, 0.03 mmol), and stirred for a day and night at 80° C. Ethyl acetate was added to the reaction liquid, followed by washing with water and saturated brine and drying over anhydrous sodium sulfate. Concentrating the reaction liquid under reduced pressure, the residue was purified on silica gel column chromatography (C-300; methanol:chloroform=1:20-1:10) to provide the title compound (6 mg, 53%) as a white solid.

Source