[6-羟基-2-(4-羟基苯基)-苯并噻吩-3-基]-[4-[2-(1-哌啶)乙氧基]苯基]-甲酮合成路线 (共 14 条)
反应条件
1: With boron trichloride in dichloromethane T=2 - 20°C; 52.25 h; 2: With methanol in dichloromethane T=12°C; 1.08333 h; Reflux; Product distribution / selectivity;
参考文献
Hexal AG
Patent: EP2322519 A1, 2011 ;
Location in patent: Page/Page column 34 ;
反应条件
1: With sodium hydroxide in dichloromethane; water
T=17°C; 0.25 h;
2: With hydrogenchloride in methanol; dichloromethane; water
T=45 - 50°C; pH=1.5;
参考文献
Hexal AG
Patent: EP2322519 A1, 2011 ;
Location in patent: Page/Page column 28 ;
反应条件
tetrabutylammomium bromide; sodium hydroxide in methanol; dichloromethane; water
T=20°C; 16 h; Product distribution / selectivity;
参考文献
Hexal AG
Patent: EP2314581 A1, 2011 ;
Location in patent: Page/Page column 46-48 ;
反应条件
aluminium trichloride in dichloromethane
T=27 - 29°C; 1.5 h; Yield given;
参考文献
Jones, Charles D.; Jevnikar, Mary G.; Pike, Andrew J.; Peters, Mary K.; Black, Larry J.; at al.
Journal of Medicinal Chemistry, 1984 , vol. 27, # 8 p. 1057 - 1066
反应条件
1: 80.4 percent / KOH / ethanol; H2O; ethyl acetate / Ambient temperature
2: 69 percent / PPA / 1 h / 85 - 90 °C
3: AlCl3 / CH2Cl2 / 1.5 h / 27 - 29 °C
View Scheme
参考文献
Jones, Charles D.; Jevnikar, Mary G.; Pike, Andrew J.; Peters, Mary K.; Black, Larry J.; at al.
Journal of Medicinal Chemistry, 1984 , vol. 27, # 8 p. 1057 - 1066
反应条件
1: 69 percent / PPA / 1 h / 85 - 90 °C
2: AlCl3 / CH2Cl2 / 1.5 h / 27 - 29 °C
View Scheme
参考文献
Jones, Charles D.; Jevnikar, Mary G.; Pike, Andrew J.; Peters, Mary K.; Black, Larry J.; at al.
Journal of Medicinal Chemistry, 1984 , vol. 27, # 8 p. 1057 - 1066
反应条件
1: SOCl2, DMF / toluene
2: AlCl3 / CH2Cl2 / 1.5 h / 27 - 29 °C
View Scheme
参考文献
Jones, Charles D.; Jevnikar, Mary G.; Pike, Andrew J.; Peters, Mary K.; Black, Larry J.; at al.
Journal of Medicinal Chemistry, 1984 , vol. 27, # 8 p. 1057 - 1066
反应条件
1: 80.4 percent / KOH / ethanol; H2O; ethyl acetate / Ambient temperature
2: 69 percent / PPA / 1 h / 85 - 90 °C
3: AlCl3 / CH2Cl2 / 1.5 h / 27 - 29 °C
View Scheme
参考文献
Jones, Charles D.; Jevnikar, Mary G.; Pike, Andrew J.; Peters, Mary K.; Black, Larry J.; at al.
Journal of Medicinal Chemistry, 1984 , vol. 27, # 8 p. 1057 - 1066
反应条件
1.1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / ethyl acetate; water / 13 - 35 °C / Reflux
2.1: formic acid; sulfuric acid / acetic acid
3.1: thionyl chloride / N,N-dimethyl-formamide / toluene / 5 h / 65 - 70 °C
4.1: iron(III) sulfate pentahydrate; iron / toluene / 99 - 114 °C
4.2: 62 - 66 °C / Inert atmosphere
5.1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / 6 h / Reflux
5.2: 20 °C
6.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 16 h / 20 °C
6.2: 2 - 51 °C
View Scheme
参考文献
HEXAL AKTIENGESELLSCHAFT; SCHICKANEDER, Christian; SCHAeFER, Juergen
Patent: WO2011/47877 A1, 2011 ;
反应条件
1.1: formic acid; sulfuric acid / acetic acid
2.1: thionyl chloride / N,N-dimethyl-formamide / toluene / 5 h / 65 - 70 °C
3.1: iron(III) sulfate pentahydrate; iron / toluene / 99 - 114 °C
3.2: 62 - 66 °C / Inert atmosphere
4.1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / 6 h / Reflux
4.2: 20 °C
5.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 16 h / 20 °C
5.2: 2 - 51 °C
View Scheme
参考文献
HEXAL AKTIENGESELLSCHAFT; SCHICKANEDER, Christian; SCHAeFER, Juergen
Patent: WO2011/47877 A1, 2011 ;