6-甲氧基-苯并[b]噻吩-3-羧酸合成路线 （共 9 条）
反应条件
1: With water; potassium hydroxide in tetrahydrofuran
T=20°C; Cooling;
2: With hydrogenchloride in water; ethyl acetate
pH=3;
参考文献
SMITHKLINE BEECHAM CORPORATION
Patent: WO2008/157270 A1, 2008 ;
Location in patent: Page/Page column 95 ;
反应条件
1: SnCl4 / 1,2-dichloro-ethane / 0 - 20 °C
2: aq. NaOH; Br2 / dioxane / 0 - 20 °C
3: CuBr; Cu / methanol / Heating
View Scheme
参考文献
Mitsumori, Susumu; Tsuri, Tatsuo; Honma, Tsunetoshi; Hiramatsu, Yoshiharu; Okada, Toshihiko; Hashizume, Hiroshi; Inagaki, Masanao; Arimura, Akinori; Yasui, Kiyoshi; Asanuma, Fujio; Kishino, Junji; Ohtani, Mitsuaki
Journal of Medicinal Chemistry, 2003 , vol. 46, # 12 p. 2446 - 2455
反应条件
1: NaOMe / methanol / Heating
2: PPA / chlorobenzene / Heating
3: SnCl4 / 1,2-dichloro-ethane / 0 - 20 °C
4: aq. NaOH; Br2 / dioxane / 0 - 20 °C
5: CuBr; Cu / methanol / Heating
View Scheme
参考文献
Mitsumori, Susumu; Tsuri, Tatsuo; Honma, Tsunetoshi; Hiramatsu, Yoshiharu; Okada, Toshihiko; Hashizume, Hiroshi; Inagaki, Masanao; Arimura, Akinori; Yasui, Kiyoshi; Asanuma, Fujio; Kishino, Junji; Ohtani, Mitsuaki
Journal of Medicinal Chemistry, 2003 , vol. 46, # 12 p. 2446 - 2455
反应条件
1: PPA / chlorobenzene / Heating
2: SnCl4 / 1,2-dichloro-ethane / 0 - 20 °C
3: aq. NaOH; Br2 / dioxane / 0 - 20 °C
4: CuBr; Cu / methanol / Heating
View Scheme
参考文献
Mitsumori, Susumu; Tsuri, Tatsuo; Honma, Tsunetoshi; Hiramatsu, Yoshiharu; Okada, Toshihiko; Hashizume, Hiroshi; Inagaki, Masanao; Arimura, Akinori; Yasui, Kiyoshi; Asanuma, Fujio; Kishino, Junji; Ohtani, Mitsuaki
Journal of Medicinal Chemistry, 2003 , vol. 46, # 12 p. 2446 - 2455
反应条件
1: aq. NaOH; Br2 / dioxane / 0 - 20 °C
2: CuBr; Cu / methanol / Heating
View Scheme
参考文献
Mitsumori, Susumu; Tsuri, Tatsuo; Honma, Tsunetoshi; Hiramatsu, Yoshiharu; Okada, Toshihiko; Hashizume, Hiroshi; Inagaki, Masanao; Arimura, Akinori; Yasui, Kiyoshi; Asanuma, Fujio; Kishino, Junji; Ohtani, Mitsuaki
Journal of Medicinal Chemistry, 2003 , vol. 46, # 12 p. 2446 - 2455
反应条件
copper; copper(I) bromide in methanol
Heating;
参考文献
Mitsumori, Susumu; Tsuri, Tatsuo; Honma, Tsunetoshi; Hiramatsu, Yoshiharu; Okada, Toshihiko; Hashizume, Hiroshi; Inagaki, Masanao; Arimura, Akinori; Yasui, Kiyoshi; Asanuma, Fujio; Kishino, Junji; Ohtani, Mitsuaki
Journal of Medicinal Chemistry, 2003 , vol. 46, # 12 p. 2446 - 2455
反应条件
1.1: AlCl3, aluminium chloride / dichloromethane / 1.25 h / -75 - -40 °C / Inert atmosphere
1.2: 1.5 h / -40 - 0 °C
2.1: potassium hydroxide; water / tetrahydrofuran / 20 °C / Cooling
2.2: pH 3
View Scheme
参考文献
SMITHKLINE BEECHAM CORPORATION
Patent: WO2008/157270 A1, 2008 ;
反应条件
1.1: potassium carbonate / acetone
2.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
2.2: 72 h / 20 °C
3.1: AlCl3, aluminium chloride / dichloromethane / 1.25 h / -75 - -40 °C / Inert atmosphere
3.2: 1.5 h / -40 - 0 °C
4.1: potassium hydroxide; water / tetrahydrofuran / 20 °C / Cooling
4.2: pH 3
View Scheme
参考文献
SMITHKLINE BEECHAM CORPORATION
Patent: WO2008/157270 A1, 2008 ;
反应条件
1.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
1.2: 72 h / 20 °C
2.1: AlCl3, aluminium chloride / dichloromethane / 1.25 h / -75 - -40 °C / Inert atmosphere
2.2: 1.5 h / -40 - 0 °C
3.1: potassium hydroxide; water / tetrahydrofuran / 20 °C / Cooling
3.2: pH 3
View Scheme
参考文献
SMITHKLINE BEECHAM CORPORATION
Patent: WO2008/157270 A1, 2008 ;
