2-溴-1,3,5-三甲基苯合成路线 （共 240 条）
反应条件
1: 4-trifluoromethylphenyltitanium triisopropoxide With N-(diphenylphosphino)-2-phenyl-1H-indole; palladium diacetate in toluene
0.0833333 h; Inert atmosphere;
2: 2-Bromo-1,3,5-trimethyl-benzene in toluene
T=90°C; 1 h; Inert atmosphere;
参考文献
Lee, Hang Wai; Lam, Fuk Loi; So, Chau Ming; Lau, Chak Po; Chan, Albert S. C.; Kwong, Fuk Yee
Angewandte Chemie, International Edition, 2009 , vol. 48, # 40 p. 7436 - 7439
Angewandte Chemie, 2009 , vol. 121, # 40 p. 7572 - 7575
反应条件
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / |Inert atmosphere
1.2: 0.25 h / 0 °C / |Inert atmosphere
2.1: acetonitrile-D3 / 25 °C / |Inert atmosphere
3.1: lithium chloride; [PdCl2(AsPh3)2]; triphenyl-arsane; [AuCl(AsPh3)] / acetonitrile / 24 h / 80 °C / |Inert atmosphere
View Scheme
参考文献
Delpozo, Juan; Carrasco, Desiree; Perez-Temprano, Monica H.; Garcia-Melchor, Max; Alvarez, Rosana; Casares, Juan A.; Espinet, Pablo
Angewandte Chemie - International Edition, 2013 , vol. 52, # 8 p. 2189 - 2193
Angew. Chem., 2013 , vol. 125, # 8 p. 2245 - 2249
反应条件
Zinc chloride in tetrahydrofuran
参考文献
Abbott Laboratories
Patent: US4623661 A1, 1986 ;
反应条件
bis(triphenylphosphine)palladium(II) chloride; tert.-butyl lithium; diisobutylaluminium hydride; zinc(II) chloride in tetrahydrofuran
T=-78 - 20°C; 1 h;
参考文献
Summers; Mazdiyasni; Holms; Ratajczyk; Dyer; Carter
Journal of Medicinal Chemistry, 1987 , vol. 30, # 3 p. 574 - 580
反应条件
potassium carbonate in ethanol; water
T=80°C; Suzuki-Miyaura coupling; 12 h;
参考文献
Sreedhar; Yada, Divya; Reddy, P. Surendra
Advanced Synthesis and Catalysis, 2011 , vol. 353, # 14-15 p. 2823 - 2836
参考文献
Augeri, David J.; Baumeister, Steven A.; Bruncko, Milan; Dickman, Daniel A.; Ding, Hong; Dinges, Jurgen; Fesik, Stephen W.; Hajduk, Philip J.; Kunzer, Aaron R.; McClellan, William; Nettesheim, David G.; Oost, Thorsten; Petros, Andrew M.; Rosenberg, Saul H.; Shen, Wang; Thomas, Sheela A.; Wang, Xilu; Wendt, Michael D.
Patent: US2002/86887 A1, 2002 ;
US 20020086887 A1
反应条件
1: 52 percent / 1.) a) tert-butyllithium, zinc chloride, b) diisobutylaluminium hydride, palladium bis(triphenylphosphine) dichloride / tetrahydrofuran / 1 h / -78 - 20 °C
2: LiOH / propan-2-ol; H2O
View Scheme
参考文献
Summers; Mazdiyasni; Holms; Ratajczyk; Dyer; Carter
Journal of Medicinal Chemistry, 1987 , vol. 30, # 3 p. 574 - 580
反应条件
1: 1.) Mg / 1.) THF, 2.) THF, -40 deg C to -50 deg C, 1.5h
2: 49 percent / 1.68N HCl / diethyl ether
3: 1.) 1.5N n-butyllithium / 1.) THF, hexane, 2.) 20h, RT
4: 73 percent Spectr. / 2.14N HCl / tetrahydrofuran; diethyl ether
5: 63 percent / DBU / tetrahydrofuran / 1.) RT, 2.5h, 2.) 20h
View Scheme
参考文献
Knaap, Th.A. van der; Klebach, Th.C.; Visser, F.; Bickelhaupt, F.; Ros, P.; et al.
Tetrahedron, 1984 , vol. 40, # 4 p. 765 - 776
反应条件
Yield given. Multistep reaction;
参考文献
Knaap, Th.A. van der; Klebach, Th.C.; Visser, F.; Bickelhaupt, F.; Ros, P.; et al.
Tetrahedron, 1984 , vol. 40, # 4 p. 765 - 776
反应条件
palladium diacetate; P(i-BuNCH2CH2)3N; sodium t-butanolate in toluene
T=80°C;
参考文献
Urgaonkar, Sameer; Nagarajan; Verkade
Journal of Organic Chemistry, 2003 , vol. 68, # 2 p. 452 - 459
