Реакция #43334

Уравнение реакции

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

Выход 100.0%

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

Выход 100.0%

Растворители

THF

DMF

brine

Условия реакции

Обработка

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

Методика

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%).

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