반응 #43334

반응 방정식

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

수율 100.0%

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

수율 100.0%

용매

THF

DMF

brine

반응 조건

후처리

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

실험 절차

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%).

출처