1-(四氢-2H-吡喃-2-基)-4-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-1H-吲唑合成路线 （共 12 条）
反应条件
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate in 1,4-dioxane; dichloromethane
3 h; Inert atmosphereReflux;
参考文献
Crestey, Francois; Lohou, Elodie; Stiebing, Silvia; Collot, Valerie; Rault, Sylvain
Synlett, 2009 , # 4 p. 615 - 619
反应条件
potassium acetate; bis-triphenylphosphine-palladium(II) chloride; tri-cyclo-hexyl-phosphine in dimethyl sulfoxide
T=130°C; 16 h; Product distribution / selectivity;
参考文献
GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG
Patent: WO2009/146406 A1, 2009 ;
Location in patent: Page/Page column 66-67 ;
WO 2009/146406 A1
反应条件
potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in dimethyl sulfoxide
T=80°C; 2 - 3 h; Product distribution / selectivity;
参考文献
GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG
Patent: WO2009/146406 A1, 2009 ;
Location in patent: Page/Page column 68-69 ;
WO 2009/146406 A1
反应条件
1: 3,4-dihydro-2H-pyran; 4-chloro-1H-indazole With pyridinium p-toluenesulfonate in n-heptane; toluene
T=40°C; 11 h; Inert atmosphereLarge scale;
2: 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane With Ni(NO3)2·6H2O; triethylamine; triphenylphosphine in methanol
T=0 - 25°C; 3.5 h; Inert atmosphereLarge scale;
参考文献
Tian, Qingping; Cheng, Zhigang; Yajima, Herbert M.; Savage, Scott J.; Green, Keena L.; Humphries, Theresa; Reynolds, Mark E.; Babu, Srinivasan; Gosselin, Francis; Askin, David; Kurimoto, Isao; Hirata, Norihiko; Iwasaki, Mitsuhiro; Shimasaki, Yasuharu; Miki, Takashi
Organic Process Research and Development, 2013 , vol. 17, # 1 p. 97 - 107
反应条件
triethylamine; triphenylphosphine; (1,5-cyclooctadiene)(cyclopentadienyl)nickel in methanol
T=25 - 70°C; 4 h; Inert atmosphere; Product distribution / selectivity;
参考文献
GENENTECH, INC.; SUMITOMO CHEMICAL COMPANY, LIMITED
Patent: US2012/123122 A1, 2012 ;
Location in patent: Page/Page column 12 ;
反应条件
1.1: potassium acetate / chloroform / 0 °C
1.2: 1 h / 25 °C
2.1: pyridinium p-toluenesulfonate / dichloromethane / 16 h / 45 °C
3.1: potassium acetate / tri-cyclo-hexyl-phosphine; bis-triphenylphosphine-palladium(II) chloride / dimethyl sulfoxide / 16 h / 130 °C
View Scheme
参考文献
F. HOFFMANN-LA-ROCHE AG; DOTSON, Jennafer; HEALD, Robert Andrew; HEFFRON, Timothy; JONES, Graham Elgin; KRINTEL, Sussie Lerche; MCLEAN, Neville James; NDUBAKU, Chudi; OLIVERO, Alan G.; SALPHATI, Laurent; WANG, Lan; WEI, BinQing
Patent: WO2012/82997 A1, 2012 ;
WO 2012/082997 A1
反应条件
1: pyridinium p-toluenesulfonate / dichloromethane / 16 h / 45 °C
2: potassium acetate / tri-cyclo-hexyl-phosphine; bis-triphenylphosphine-palladium(II) chloride / dimethyl sulfoxide / 16 h / 130 °C
View Scheme
参考文献
F. HOFFMANN-LA-ROCHE AG; DOTSON, Jennafer; HEALD, Robert Andrew; HEFFRON, Timothy; JONES, Graham Elgin; KRINTEL, Sussie Lerche; MCLEAN, Neville James; NDUBAKU, Chudi; OLIVERO, Alan G.; SALPHATI, Laurent; WANG, Lan; WEI, BinQing
Patent: WO2012/82997 A1, 2012 ;
WO 2012/082997 A1
反应条件
1: hydrogen / palladium 10 on activated carbon / ethanol
2: pyridinium p-toluenesulfonate / dichloromethane / 2 h / 50 °C
3: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 80 °C
View Scheme
参考文献
F. HOFFMANN-LA-ROCHE AG; DOTSON, Jennafer; HEALD, Robert Andrew; HEFFRON, Timothy; JONES, Graham Elgin; KRINTEL, Sussie Lerche; MCLEAN, Neville James; NDUBAKU, Chudi; OLIVERO, Alan G.; SALPHATI, Laurent; WANG, Lan; WEI, BinQing
Patent: WO2012/82997 A1, 2012 ;
WO 2012/082997 A1
反应条件
1: sodium nitrite / water; acetic acid / 15 - 30 °C
2: hydrogen / palladium 10 on activated carbon / ethanol
3: pyridinium p-toluenesulfonate / dichloromethane / 2 h / 50 °C
4: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 80 °C
View Scheme
参考文献
F. HOFFMANN-LA-ROCHE AG; DOTSON, Jennafer; HEALD, Robert Andrew; HEFFRON, Timothy; JONES, Graham Elgin; KRINTEL, Sussie Lerche; MCLEAN, Neville James; NDUBAKU, Chudi; OLIVERO, Alan G.; SALPHATI, Laurent; WANG, Lan; WEI, BinQing
Patent: WO2012/82997 A1, 2012 ;
WO 2012/082997 A1
反应条件
1: pyridinium p-toluenesulfonate / dichloromethane / 2 h / 50 °C
2: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 80 °C
View Scheme
参考文献
F. HOFFMANN-LA-ROCHE AG; DOTSON, Jennafer; HEALD, Robert Andrew; HEFFRON, Timothy; JONES, Graham Elgin; KRINTEL, Sussie Lerche; MCLEAN, Neville James; NDUBAKU, Chudi; OLIVERO, Alan G.; SALPHATI, Laurent; WANG, Lan; WEI, BinQing
Patent: WO2012/82997 A1, 2012 ;
WO 2012/082997 A1
