4-溴-1-三异丙基甲硅烷基-1H-吡咯并[2,3-b]吡啶合成路线 （共 10 条）
反应条件
1.1: n-butyllithium / diethyl ether / -78 °C 1.2: 66 percent / N-fluorobenzenesulfonimide / tetrahydrofuran / -78 °C 2.1: 100 percent / TBAF / tetrahydrofuran / 20 °C View Scheme
参考文献
Thibault, Carl; L'Heureux, Alexandre; Bhide, Rajeev S.; Ruel, Rejean
Organic Letters, 2003 , vol. 5, # 26 p. 5023 - 5025
反应条件
1.1: n-butyllithium / hexane; diethyl ether / 1.25 h / -78 - -5 °C / |Inert atmosphere 1.2: 3 h / -78 °C 2.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C 2.2: 1 h / -78 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C 4.1: nitric acid / 0.5 h / 0 °C View Scheme
参考文献
VERNALIS (RandD) LIMITED; STOKES, Stephen; GRAHAM, Christoper John; RAY, Stuart Christopher; STEFANIAK, Emma Jayne
Patent: WO2013/114113 A1, 2013 ;
反应条件
1.1: n-butyllithium / hexane; diethyl ether / 1.25 h / -78 - -5 °C / |Inert atmosphere 1.2: 3 h / -78 °C 2.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C 2.2: 1 h / -78 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C View Scheme
参考文献
VERNALIS (RandD) LIMITED; STOKES, Stephen; GRAHAM, Christoper John; RAY, Stuart Christopher; STEFANIAK, Emma Jayne
Patent: WO2013/114113 A1, 2013 ;
反应条件
1: With n-butyllithium; boric acid trimethyl ester in tetrahydrofuran T=-78°C; 2: With water; ammonium chloride in tetrahydrofuran
参考文献
ABBOTT LABORATORIES
Patent: US2009/258907 A1, 2009 ;
Location in patent: Page/Page column 20 ;
US 20090258907 A1
反应条件
sodium hydride in tetrahydrofuran
T=80°C; 3 h;
参考文献
Thibault, Carl; L'Heureux, Alexandre; Bhide, Rajeev S.; Ruel, Rejean
Organic Letters, 2003 , vol. 5, # 26 p. 5023 - 5025
反应条件
1: 4-bromo-7-azaindole With sodium hydride in tetrahydrofuran
T=0°C; 0.25 h;
2: triisopropylsilyl chloride in tetrahydrofuran
T=80°C; 3.5 h;
参考文献
DEVGEN N.V.
Patent: WO2007/42321 A2, 2007 ;
Location in patent: Page/Page column 50-51 ;
WO 2007/042321 A2
反应条件
1: 54 percent / tetramethylammonium bromide; methanesulfonic anhydride / dimethylformamide / 4 h / 0 - 23 °C
2: 99 percent / sodium hydride / tetrahydrofuran / 3 h / 80 °C
View Scheme
参考文献
Thibault, Carl; L'Heureux, Alexandre; Bhide, Rajeev S.; Ruel, Rejean
Organic Letters, 2003 , vol. 5, # 26 p. 5023 - 5025
反应条件
1: With tert.-butyl lithium in tetrahydrofuran; pentane
T=-85°C; 0.25 h;
2: With iodine in tetrahydrofuran; pentane
0.833333 h;
参考文献
DEVGEN N.V.
Patent: WO2007/42321 A2, 2007 ;
Location in patent: Page/Page column 51 ;
WO 2007/042321 A2
反应条件
1.1: n-butyllithium / diethyl ether / -78 °C
1.2: 66 percent / N-fluorobenzenesulfonimide / tetrahydrofuran / -78 °C
2.1: 24 percent / triethylamine; NMP / 2 h / 160 °C / microwave irradiation
View Scheme
参考文献
Caldwell, John J.; Cheung, Kwai-Ming; Collins, Ian
Tetrahedron Letters, 2007 , vol. 48, # 9 p. 1527 - 1529
反应条件
1: With tert.-butyl lithium in tetrahydrofuran; pentane
T=-78°C;
2: With N-fluoro-N-(phenylsulfonyl)benzene-sulfonamide in tetrahydrofuran; pentane
T=-78°C; 2 h;
参考文献
ARRAY BIOPHARMA INC.
Patent: WO2009/140320 A1, 2009 ;
Location in patent: Page/Page column 86-87 ;
WO 2009/140320 A1
