2-硼-4-甲氧基-1H-吲哚-1-羧酸-1-(1,1-二甲基乙基)酯合成路线 （共 8 条）
反应条件
1: With lithium diisopropyl amide in tetrahydrofuran; n-heptane; ethylbenzene; toluene T=-2 - 3°C; 1.5 h; Industry scale; 2: With hydrogenchloride; water in tetrahydrofuran; n-heptane; ethylbenzene; toluene T=15°C; 1 h; Industry scale;
参考文献
CEPHALON, INC.; BIERLMAIER, Stephen; CHRISTIE, Michael; COURVOISIER, Laurent; FIELD, R. Scott; HALTIWANGER, R. Curtis; HE, Linli; JACOBS, Martin J.; KRESS, Michael; MCKEAN, Robert E.; MOWREY, Dale R.; PETRAITIS, Joseph; YAZDANIAN, Mehran
Patent: WO2011/28580 A1, 2011 ;
Location in patent: Page/Page column 19; 20; 21 ;
反应条件
hydrogenchloride; water in tetrahydrofuran 0.0333333 h;
参考文献
BIOVITRUM AB (PUBL)
Patent: WO2007/147874 A1, 2007 ;
Location in patent: Page/Page column 148-149 ;
WO 2007/147874 A1
反应条件
1: With tri-isopropoxy-borane; lithium diisopropyl amide in tetrahydrofuran T=0 - 5°C; Inert atmosphere; 2: With hydrogenchloride in tetrahydrofuran; water
参考文献
Zhou, Jiao-Long; Ye, Meng-Chun; Sun, Xiu-Li; Tang, Yong
Tetrahedron, 2009 , vol. 65, # 34 p. 6877 - 6881
反应条件
1.1: 4-(N,N-dimethlyamino)pyridine / toluene / 40 °C / Industry scale 1.2: 2.75 h / 40 - 41 °C / Industry scale 2.1: lithium diisopropyl amide / n-heptane; toluene; tetrahydrofuran; ethylbenzene / 1.5 h / -2 - 3 °C / Industry scale 2.2: 1 h / 15 °C / Industry scale View Scheme
参考文献
SANOFI; ARNAUD, Joëlle; ARTIAGA, Martine; BARTH, Francis; HORTALA, Laurent; MARTINEZ, Serge; ROUX, Pascale
Patent: WO2013/87643 A1, 2013 ;
反应条件
1.1: 4-(N,N-dimethlyamino)pyridine / toluene / 40 °C / Industry scale 1.2: 2.75 h / 40 - 41 °C / Industry scale 2.1: lithium diisopropyl amide / n-heptane; toluene; tetrahydrofuran; ethylbenzene / 1.5 h / -2 - 3 °C / Industry scale 2.2: 1 h / 15 °C / Industry scale View Scheme
参考文献
CEPHALON, INC.; BIERLMAIER, Stephen; CHRISTIE, Michael; COURVOISIER, Laurent; FIELD, R. Scott; HALTIWANGER, R. Curtis; HE, Linli; JACOBS, Martin J.; KRESS, Michael; MCKEAN, Robert E.; MOWREY, Dale R.; PETRAITIS, Joseph; YAZDANIAN, Mehran
Patent: WO2011/28580 A1, 2011 ;
反应条件
1: N,N-dimethyl-formamide / 3 h / |Reflux 2: zinc; acetic acid; hydrogenchloride / water / 0.5 h / 20 °C 3: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 20 °C 4: lithium diisopropyl amide / tetrahydrofuran / 1 h / 0 - 20 °C View Scheme
参考文献
SANOFI; ARNAUD, Joëlle; ARTIAGA, Martine; BARTH, Francis; HORTALA, Laurent; MARTINEZ, Serge; ROUX, Pascale
Patent: WO2013/87643 A1, 2013 ;
反应条件
1: zinc; acetic acid; hydrogenchloride / water / 0.5 h / 20 °C 2: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 20 °C 3: lithium diisopropyl amide / tetrahydrofuran / 1 h / 0 - 20 °C View Scheme
参考文献
SANOFI; ARNAUD, Joëlle; ARTIAGA, Martine; BARTH, Francis; HORTALA, Laurent; MARTINEZ, Serge; ROUX, Pascale
Patent: WO2013/87643 A1, 2013 ;
反应条件
1.1: N,N-dicyclohexylamine / triphenylphosphine; palladium diacetate / toluene / 0.42 h / 20 °C / Industry scale; Inert atmosphere
1.2: 18.4 - 22.3 °C / Industry scale; Inert atmosphere
2.1: sodium methylate / toluene; methanol / 4 h / 40 - 50 °C / Industry scale
2.2: 16 h / Industry scale
3.1: acetic acid / toluene / 950 h / 10 - 33 °C / Industry scale
4.1: chloranil / tetrahydrofuran / 22 h / 60 - 70 °C / Industry scale
View Scheme
参考文献
CEPHALON, INC.; BIERLMAIER, Stephen; CHRISTIE, Michael; COURVOISIER, Laurent; FIELD, R. Scott; HALTIWANGER, R. Curtis; HE, Linli; JACOBS, Martin J.; KRESS, Michael; MCKEAN, Robert E.; MOWREY, Dale R.; PETRAITIS, Joseph; YAZDANIAN, Mehran
Patent: WO2011/28580 A1, 2011 ;
