反応 #43334

反応方程式

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

収率 100.0%

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

収率 100.0%

溶媒

THF

DMF

brine

反応条件

後処理

1. 1
   その他To the reaction liquid
2. 2
   workup.STIRRINGstirred at 100° C. for 19 hours
3. 3
   抽出followed by extraction with ethyl acetate
4. 4
   乾燥drying over anhydrous magnesium sulfate
5. 5
   濃縮Concentrating the solvent under reduced pressure
6. 6
   その他the residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:9-1:4)

実験手順

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%).

出典