5-甲氧基吲哚-2-羧酸合成路线 （共 29 条）
反应条件
1: 89 percent / thionyl chloride / 4 h / Heating 2: 98 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 1.5 h / Heating 3: 60 percent / CrO3, pyridine / CH2Cl2 / 19 h / Ambient temperature View Scheme
参考文献
Sumitomo Pharmaceuticals Company, Limited
Patent: EP1479384 A1, 2004 ;
反应条件
1: 5-methoxy-1H-indole-2-carboxylic acid With 1,1'-carbonyldiimidazole in dichloromethane T=0°C; 2: dimethyl amine in tetrahydrofuran; dichloromethane T=20°C; Sealed tube;
参考文献
WYETH LLC; AYRAL-KALOUSTIAN, Semiramis; MANSOUR, Tarek Suhayl; TSOU, Hwei-Ru; ZHANG, Nan; VENKATESAN, Aranapakam M.; DI, Li; KERNS, Edward H.
Patent: WO2010/30727 A1, 2010 ;
Location in patent: Page/Page column 99-100 ;
WO 2010/030727 A1
反应条件
1: thionyl chloride / benzene / 5.92 h / 20 - 55 °C 2: benzene; diethyl ether / Ambient temperature View Scheme
参考文献
Pelaprat, Didier; Oberlin, Robert; Le Guen, Irene; Roques, Bernard P.; Pecq, Jean-Bernard Le
Journal of Medicinal Chemistry, 1980 , vol. 23, # 12 p. 1330 - 1335
反应条件
1: 5-methoxy-1H-indole-2-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane T=0°C; 0.5 h; 2: 1-methyl-piperazine in dichloromethane T=20°C;
参考文献
WYETH LLC; AYRAL-KALOUSTIAN, Semiramis; MANSOUR, Tarek Suhayl; TSOU, Hwei-Ru; ZHANG, Nan; VENKATESAN, Aranapakam M.; DI, Li; KERNS, Edward H.
Patent: WO2010/30727 A1, 2010 ;
Location in patent: Page/Page column 103 ;
WO 2010/030727 A1
反应条件
sulfuric acid 6 h; Reflux;
参考文献
WO2012/59776 A1, ;
Page/Page column 57 ;
WO 2012/059776 A1
反应条件
sodium hydrogencarbonate in N,N-dimethyl-formamide 28 h; Ambient temperature;
参考文献
Bioorganic and Medicinal Chemistry, , vol. 5, # 3 p. 507 - 514
反应条件
1: 77 percent / Cu; quinoline / Heating 2: 90 percent / phosphoryl chloride / 0 - 40 °C View Scheme
参考文献
Coowar, Djalil; Bouissac, Julien; Hanbali, Mazen; Paschaki, Marie; Mohier, Eliane; Luu, Bang
Journal of Medicinal Chemistry, 2004 , vol. 47, # 25 p. 6270 - 6282
反应条件
in quinoline 0.2 h; microwave;
参考文献
Jones, Graham B.; Chapman, Brant J.
Journal of Organic Chemistry, 1993 , vol. 58, # 20 p. 5558 - 5559
反应条件
1.1: 77 percent / Cu; quinoline / Heating
2.1: 90 percent / phosphoryl chloride / 0 - 40 °C
3.1: NaOH / CH2Cl2 / 20 °C
3.2: 95 percent / CH2Cl2 / 20 °C
View Scheme
参考文献
Coowar, Djalil; Bouissac, Julien; Hanbali, Mazen; Paschaki, Marie; Mohier, Eliane; Luu, Bang
Journal of Medicinal Chemistry, 2004 , vol. 47, # 25 p. 6270 - 6282
反应条件
1.1: 77 percent / Cu; quinoline / Heating
2.1: 90 percent / phosphoryl chloride / 0 - 40 °C
3.1: NaOH / CH2Cl2 / 20 °C
3.2: 95 percent / CH2Cl2 / 20 °C
4.1: n-BuLi / tetrahydrofuran; hexane / 0 °C
4.2: potassium tert-butoxide / tetrahydrofuran; hexane / 0 °C
4.3: 65 percent / tetrahydrofuran; hexane / -78 - 0 °C
5.1: 91 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr
View Scheme
参考文献
Coowar, Djalil; Bouissac, Julien; Hanbali, Mazen; Paschaki, Marie; Mohier, Eliane; Luu, Bang
Journal of Medicinal Chemistry, 2004 , vol. 47, # 25 p. 6270 - 6282
