2′-羟基-5′-溴苯乙酮合成路线 （共 81 条）
反应条件
1.1: LHMDS / tetrahydrofuran / 2.5 h / -78 - -20 °C
1.2: tetrahydrofuran / 3 h / -78 - 20 °C
1.3: 94 percent / AcOH; H2SO4 / tetrahydrofuran / 0.08 h / 120 °C
2.1: 37 percent / NaOtBu / Pd2(dba)3; BINAP / toluene / 1 h / 80 °C / microwave irradiation
View Scheme
参考文献
Fitzmaurice, Richard J.; Etheridge, Zac C.; Jumel, Emelie; Woolfson, Derek N.; Caddick, Stephen
Chemical Communications, 2006 , # 46 p. 4814 - 4816
反应条件
1: With pyrrolidine in methanol
T=80°C; 16 h;
2: With hydrogenchloride in 1,4-dioxane; dichloromethane
T=20°C; 16 h;
参考文献
UNIVERSITY HEALTH NETWORK; PAULS, Heinz W.; LAUFER, Radoslaw; LIU, Yong; LI, Sze-Wan; FORREST, Bryan T.; LANG, Yunhui; PATEL, Narendra Kumar B.; EDWARDS, Louise G.; NG, Grace; SAMPSON, Peter Brent; FEHER, Miklos; AWREY, Donald E.
Patent: WO2013/53051 A1, 2013 ;
Location in patent: Page/Page column 93 ;
反应条件
1: 89 percent / POCl2 / pyridine / 3 h / 60 - 70 °C
2: 64 percent / NaH / tetrahydrofuran / 3.5 h / Heating
3: 63 percent / p-toluenesulfonic acid / dimethylsulfoxide / 80 - 90 °C
View Scheme
参考文献
Barros, Ana I. R. N. A.; Silva, Artur M. S.
Monatshefte fur Chemie, 2006 , vol. 137, # 12 p. 1505 - 1528
反应条件
tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate in benzene
4 h; Ambient temperature;
参考文献
Sabitha, G.; Rao, A. V. Subba
Synthetic Communications, 1987 , vol. 17, # 3 p. 341 - 354
反应条件
acetic anhydride; triethylamine
16 h; Heating;
参考文献
Sangwan; Verma; Malik; Dhindsa
Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry, 1990 , vol. 29, # 3 p. 294 - 296
反应条件
pyrrolidine in toluene
Reflux;
参考文献
ARRAY BIOPHARMA INC.; ALLEN, Shelley; ANDREWS, Steven, Wade; BLAKE, James, F.; BRANDHUBER, Barbara, J.; HAAS, Julia; JIANG, Yutong; KERCHER, Timothy; KOLAKOWSKI, Gabrielle, R.; THOMAS, Allen, A.; WINSKI, Shannon, L.
Patent: WO2014/78454 A1, 2014 ;
Location in patent: Paragraph 00850 ;
反应条件
potassium tert-butylate in toluene
T=25°C;
参考文献
Leahy, Justin J.J.; Golding, Bernard T.; Griffin, Roger J.; Hardcastle, Ian R.; Richardson, Caroline; Rigoreau, Laurent; Smith, Graeme C.M.
Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 24 p. 6083 - 6087
反应条件
1.1: t-BuOK / tetrahydrofuran / 16 h / 20 °C
1.2: 36 percent / aq. H2SO4 / 16 h / pH 4
2.1: 64 percent / K2CO3 / acetone / 2 h / Heating
View Scheme
参考文献
Leahy, Justin J.J.; Golding, Bernard T.; Griffin, Roger J.; Hardcastle, Ian R.; Richardson, Caroline; Rigoreau, Laurent; Smith, Graeme C.M.
Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 24 p. 6083 - 6087
反应条件
1.1: potassium carbonate / acetone / 0.5 h / Inert atmosphere
1.2: Inert atmosphere; Reflux
2.1: sodium hydroxide / tetrahydrofuran / 20 °C
View Scheme
参考文献
Piemontese, Luca; Carbonara, Giuseppe; Fracchiolla, Giuseppe; Laghezza, Antonio; Tortorella, Paolo; Loiodice, Fulvio
Heterocycles, 2010 , vol. 81, # 12 p. 2865 - 2872
反应条件
palladium(II) dichloride bis[bis(diphenylphosphine)ferrocene]; triethylamine
T=100°C;
参考文献
BIOENERGENIX; MCCALL, John; KELLY, Robert, C.; ROMERO, Donna, L.
Patent: WO2014/66795 A1, 2014 ;
Location in patent: Paragraph 0175 ;
