反应详情

温度

98 °C

A mixture of ethyl (3-{3-[5-(2-bromophenyl)-2-oxopyridin-1(2H)-yl]propyl}phenoxy)acetate (235 mg), (2-methoxyphenyl)boronic acid (114 mg), Na2CO3(159 mg), Pd(PPh3)4 (29 mg) in toluene (8 mL) and water (4 mL) was stirred under N2 gas atmosphere at 98° C. for 30 hours and cooled to ambient temperature. The reaction mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The aqueous layer of the reaction mixture was acidified with 1M HCl aqueous solution and extracted with EtOAc and the organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The filtrate and the residue of the first extract was combined and evaporated in vacuo. The residue was dissolved in EtOH (20 mL). To the solution was added concentrated H2SO4 (1.5 mL) at ambient temperature and refluxed for 1 hour. The reaction mixture was cooled to ambient temperature, neutralized with saturated NaHCO3 aqueous solution and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=60:40) to afford ethyl (3-{3-[5-(2′-methoxybiphenyl-2-yl)-2-oxopyridin-1(2H)-yl]propyl}phenoxy)acetate (75 mg) as a colorless oil.

1. temperaturecooled to ambient temperature
2. extractionThe reaction mixture was extracted with EtOAc
3. washThe organic layer was washed with brine
4. dry with materialdried over anhydrous MgSO4
5. filtrationfiltered
6. customevaporated in vacuo
7. extractionextracted with EtOAc
8. washthe organic layer was washed with brine
9. dry with materialdried over anhydrous MgSO4
10. filtrationfiltered
11. customevaporated in vacuo
12. extractionThe filtrate and the residue of the first extract
13. customevaporated in vacuo
14. dissolutionThe residue was dissolved in EtOH (20 mL)
15. additionTo the solution was added concentrated H2SO4 (1.5 mL) at ambient temperature
16. temperaturerefluxed for 1 hour
17. temperatureThe reaction mixture was cooled to ambient temperature
18. extractionextracted with EtOAc
19. washThe organic layer was washed with brine
20. dry with materialdried over anhydrous MgSO4
21. filtrationfiltered
22. customevaporated in vacuo
23. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=60:40)