Reaktion #43334

Reaktionsgleichung

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

Ausbeute 100.0%

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

Ausbeute 100.0%

Lösungsmittel

THF

DMF

brine

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle