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 N-fluoro-N-(phenylsulfonyl)benzene-sulfonamide 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 iodine in tetrahydrofuran; cyclohexane T=-78°C; 0.75 h;
参考文献
VERNALIS (RandD) LIMITED; STOKES, Stephen; GRAHAM, Christoper John; RAY, Stuart Christopher; STEFANIAK, Emma Jayne
Patent: WO2013/114113 A1, 2013 ;
Location in patent: Page/Page column 135; 136 ;
反应条件
1: 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine With n-butyllithium in tetrahydrofuran T=-78°C; 1.5 h; 2: iodine in tetrahydrofuran T=-78 - 0°C; 1 h;
参考文献
Heinrich, Timo; Seenisamy, Jeyaprakashnarayanan; Emmanuvel, Lourdusamy; Kulkarni, Santosh S.; Bomke, Joerg; Rohdich, Felix; Greiner, Hartmut; Esdar, Christina; Krier, Mireille; Graedler, Ulrich; Musil, Djordje
Journal of Medicinal Chemistry, 2013 , vol. 56, # 3 p. 1160 - 1170
反应条件
1.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C 1.2: 0.75 h / -78 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 3.2: 2 h / 20 °C 4.1: copper(l) iodide / N,N-dimethyl-formamide / 2.5 h / 100 °C 5.1: lithium hydroxide hydrate / water; tetrahydrofuran / 64 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 sec.-butyllithium in tetrahydrofuran; cyclohexane T=-78°C; 0.5 h; 2: With iodine in tetrahydrofuran; cyclohexane T=-78°C; 0.333333 h; 3: With tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C; 0.166667 h;
参考文献
ARRAY BIOPHARMA INC.
Patent: WO2009/140320 A1, 2009 ;
Location in patent: Page/Page column 98 ;
WO 2009/140320 A1
反应条件
1.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C 1.2: 0.75 h / -78 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 3.2: 2 h / 20 °C 4.1: copper(l) iodide / N,N-dimethyl-formamide / 2.5 h / 100 °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: sec.-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C 1.2: 0.75 h / -78 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 3.2: 2 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 sec.-butyllithium in tetrahydrofuran; cyclohexane
T=-78°C; 0.5 h;
2: With 4-toluenesulfonyl azide 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 carbon tetrabromide 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: 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine With sec.-butyllithium in tetrahydrofuran; cyclohexane
T=78°C; 0.5 h; Inert atmosphere;
2: carbon tetrabromide in tetrahydrofuran; cyclohexane
2 h;
参考文献
Gehringer, Matthias; Pfaffenrot, Ellen; Bauer, Silke; Laufer, Stefan A.
ChemMedChem, 2014 , vol. 9, # 2 p. 277 - 281
