5-溴-2-三氟甲基吡啶合成路线 （共 22 条）
反应条件
1: 5-bromo-2-(trifluoromethyl)pyridine With n-butyllithium; diisopropylamine in tetrahydrofuran; hexanes T=-78 - -60°C; 0.0166667 h; Cooling with acetone-dry ice; 2: carbon dioxide in tetrahydrofuran; hexanes T=-78 - 20°C; 1 h; Cooling with acetone-dry ice; 3: With hydrogenchloride; sodium hydroxide more than 3 stages;
参考文献
NEUROCRINE BIOSCIENCES, INC.
Patent: WO2008/124610 A1, 2008 ;
Location in patent: Page/Page column 43; 44 ;
WO 2008/124610 A1
反应条件
1: 5-bromo-2-(trifluoromethyl)pyridine With n-butyllithium in hexane; toluene T=-75 - -60°C; 0.833333 h; 2: acetone in tetrahydrofuran; hexane T=-60 - -25°C; 1.25 h;
参考文献
Butcher, Kenneth J.; Denton, Steven M.; Field, Stuart E.; Gillmore, Adam T.; Harbottle, Gareth W.; Howard, Roger M.; Laity, Daniel A.; Ngono, Christian J.; Pibworth, Benjamin A.
Organic Process Research and Development, 2011 , vol. 15, # 5 p. 1192 - 1200
反应条件
1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-ethyl-N,N-diisopropylamine / 12 h / 100 °C / 2585.81 Torr 2: tetrahydrofuran / 2 h / -10 °C View Scheme
参考文献
Butcher, Kenneth J.; Denton, Steven M.; Field, Stuart E.; Gillmore, Adam T.; Harbottle, Gareth W.; Howard, Roger M.; Laity, Daniel A.; Ngono, Christian J.; Pibworth, Benjamin A.
Organic Process Research and Development, 2011 , vol. 15, # 5 p. 1192 - 1200
反应条件
in N,N-dimethyl-formamide T=65°C; 2 h;
参考文献
Ekambome Bassene, Carine; Suzenet, Franck; Hennuyer, Nathalie; Staels, Bart; Caignard, Daniel-Henri; Dacquet, Catherine; Renard, Pierre; Guillaumet, Gerald
Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 17 p. 4528 - 4532
反应条件
isopropylmagnesium chloride in tetrahydrofuran T=0°C; 2 h;
参考文献
Cottet, Fabrice; Marull, Marc; Lefebvre, Olivier; Schlosser, Manfred
European Journal of Organic Chemistry, 2003 , # 8 p. 1559 - 1568
反应条件
tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran; N,N-dimethyl-formamide T=20 - 100°C; Inert atmosphere;
参考文献
WO2010/51503 A1, ;
Page/Page column 248-249 ;
WO 2010/051503 A1
反应条件
caesium carbonate; triphenylphosphine; palladium dichloride in tetrahydrofuran; water T=75 - 80°C; 22 h; Inert atmosphere;
参考文献
WO2010/36998 A2, ;
Page/Page column 180 ;
反应条件
dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; palladium diacetate; sodium carbonate in ethanol T=85°C; Suzuki-Miyaura coupling; 16 h; Inert atmosphere;
参考文献
Ren, Wei; Li, Jingya; Zou, Dapeng; Wu, Yangjie; Wu, Yusheng
Tetrahedron, 2012 , vol. 68, # 5 p. 1351 - 1358
反应条件
1.1: 90 percent / dimethylformamide / 2 h / 65 °C
2.1: t-BuLi / tetrahydrofuran / -78 °C
2.2: 58 percent / tetrahydrofuran / 3 h / -78 °C
3.1: 65 percent / BuLi / tetrahydrofuran / 20 °C
4.1: 86 percent / H2 / Pd/C / methanol / 24 h / 20 °C / 750.06 Torr
5.1: 43 percent / BCl3; Bu4NI / CH2Cl2 / 24 h / -78 - 20 °C
View Scheme
参考文献
Ekambome Bassene, Carine; Suzenet, Franck; Hennuyer, Nathalie; Staels, Bart; Caignard, Daniel-Henri; Dacquet, Catherine; Renard, Pierre; Guillaumet, Gerald
Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 17 p. 4528 - 4532
反应条件
1: in methanol
0.166667 h;
2: With triethylamine; Pd(dppf)2Cl2 dichloromethane adduct in methanol
T=100°C; 3 h;
参考文献
SCHERING CORPORATION
Patent: WO2009/5646 A2, 2009 ;
Location in patent: Page/Page column 149-150 ;
WO 2009/005646 A2
