4-氯-1-[三(甲基乙基)硅酯]-1H-吡咯并[2,3-B]吡啶合成路线 （共 27 条）
反应条件
1: With sec.-butyllithium in tetrahydrofuran; cyclohexane
T=-78°C; 0.5 h;
2: With (R)-camphorsulfonyl oxaziridine in tetrahydrofuran; cyclohexane
T=-78°C; 0.416667 h; Further stages.;
参考文献
L'Heureux, Alexandre; Thibault, Carl; Ruel, Rejean
Tetrahedron Letters, 2004 , vol. 45, # 11 p. 2317 - 2319
反应条件
1: With sec.-butyllithium in tetrahydrofuran; cyclohexane
T=-78°C; 0.5 h;
2: With tri-isopropoxy-borane in tetrahydrofuran; cyclohexane
T=-78°C; 0.416667 h; Further stages.;
参考文献
L'Heureux, Alexandre; Thibault, Carl; Ruel, Rejean
Tetrahedron Letters, 2004 , vol. 45, # 11 p. 2317 - 2319
反应条件
1.1: sec-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C
1.2: 65 percent / (R)-camphorsulfonyl oxaziridine / tetrahydrofuran; cyclohexane / 0.42 h / -78 °C
2.1: 49 percent / zinc; acetic acid / ethyl acetate / 18 h / 20 °C
View Scheme
参考文献
L'Heureux, Alexandre; Thibault, Carl; Ruel, Rejean
Tetrahedron Letters, 2004 , vol. 45, # 11 p. 2317 - 2319
反应条件
1: 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine With sec.-butyllithium in tetrahydrofuran; hexane
T=-78°C; 0.75 h;
2: N,N-dimethyl-formamide in tetrahydrofuran; hexane
T=-78°C; 1 h;
参考文献
IRM LLC
Patent: US2010/48552 A1, 2010 ;
Location in patent: Page/Page column 10 ;
反应条件
1: 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine With sec.-butyllithium in tetrahydrofuran; hexane
T=-78°C; 0.75 h;
2: N,N-dimethyl-formamide in tetrahydrofuran; hexane
T=-78°C; 1 h;
3: With hydrogenchloride; sodium hydrogencarbonate
more than 3 stages;
参考文献
IRM LLC
Patent: WO2006/124731 A2, 2006 ;
Location in patent: Page/Page column 25-26 ;
WO 2006/124731 A2
反应条件
1: 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine With sec.-butyllithium in tetrahydrofuran; hexane; cyclohexane
T=-78°C; 0.5 h;
2: benzaldehyde in tetrahydrofuran; hexane; cyclohexane
T=20°C; 14 h;
参考文献
Pillard, Christelle; Bassene, Carine Ekambome; Suzenet, Franck; Guillaumet, Gerald
Synthesis, 2008 , # 13 p. 2049 - 2054
反应条件
1.1: sec.-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere
1.2: -78 - 20 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C
View Scheme
参考文献
BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; SCOTT, Daniel; CONLON, Patrick; JENKINS, Tracy, J.; POWELL, Noel; GUAN, Bing; CURERVO, Julio, H.; WANG, Deping; TAVERAS, Art
Patent: WO2012/58645 A1, 2012 ;
WO 2012/058645 A1
