4-溴-3-甲基苯甲酸甲酯合成路线 （共 30 条）
反应条件
lithium aluminium tetrahydride in tetrahydrofuran T=20°C; 3 h; Cooling with ice;
参考文献
CHANG, Christopher J.; VAN DE BITTNER, Genevieve V.; HIRAYAMA, Tasuku; CHAN, Jefferson
Patent: US2014/51863 A1, 2014 ;
Location in patent: Paragraph 0205; 0256-0257 ;
反应条件
hydrazine hydrate in methanol 18 h; Reflux;
参考文献
Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Wilhelm, Robert Stephen
Patent: US2011/71150 A1, 2011 ;
Location in patent: Page/Page column 33 ;
反应条件
1: 4-bromo-3-methyl-benzoic acid methyl ester With tetrakis(triphenylphosphine) palladium(0) in toluene
T=20°C; 1 h;
2: (4-cyano-phenyl)boronic acid With sodium carbonate; lithium chloride in ethanol; water; toluene
T=20°C; 50 h; Heating / reflux;
参考文献
GLAXO GROUP LIMITED
Patent: WO2004/7493 A1, 2004 ;
Location in patent: Page 29-30 ;
反应条件
1.1: chromium(VI) oxide; sulfuric acid / 1.5 h / Cooling with ice; Inert atmosphere
2.1: sulfuric acid; water / methanol / 1 h / Reflux; Inert atmosphere
2.2: 3 h / Reflux; Inert atmosphere
3.1: caesium carbonate; triphenylphosphine; palladium dichloride / tetrahydrofuran; water / 22 h / 85 °C / sealed tube; Inert atmosphere
4.1: bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate; 6-diphenylphosphinomethyl-3-methyl-2-aminopyridine / toluene / 1 h / 150 °C / Inert atmosphere
View Scheme
参考文献
Vautravers, Nicolas R.; Regent, Damien D.; Breit, Bernhard
Chemical Communications, 2011 , vol. 47, # 23 p. 6635 - 6637
反应条件
1: N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CCl4 / 2 h / 70 °C
2: 10.8 g / acetic acid / 12 h / 100 °C
3: 8.29 g / NaOH / methanol; H2O / 2 h / 20 °C
View Scheme
参考文献
Miura, Masanori; Seki, Norio; Koike, Takanori; Ishihara, Tsukasa; Niimi, Tatsuya; Hirayama, Fukushi; Shigenaga, Takeshi; Sakai-Moritani, Yumiko; Kawasaki, Tomihisa; Sakamoto, Shuichi; Okada, Minoru; Ohta, Mitsuaki; Tsukamoto, Shin-ichi
Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 23 p. 7688 - 7705
反应条件
sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in propan-1-ol; water
Heating / reflux;
参考文献
ELI LILLY AND COMPANY
Patent: WO2006/66173 A2, 2006 ;
Location in patent: Page/Page column 105-106 ;
WO 2006/066173 A2
反应条件
1: N-Boc-pyrrolidine With sec.-butyllithium; (-)-sparteine in tert-butyl methyl ether; cyclohexane
T=-78°C; 3 h;
2: With zinc(II) chloride in tetrahydrofuran; tert-butyl methyl ether; cyclohexane
T=-78 - 20°C; 1 h;
3: 4-bromo-3-methyl-benzoic acid methyl ester With palladium diacetate; [(t-Bu)3PH]BF4 in tetrahydrofuran; tert-butyl methyl ether; cyclohexane
参考文献
PFIZER PRODUCTS INC.
Patent: WO2008/53319 A1, 2008 ;
Location in patent: Page/Page column 76-77 ;
反应条件
potassium carbonate; [(P{(C6H11)3})2Pd(Cl)2] in 1,4-dioxane; water
T=100°C; Suzuki-Miyura coupling; 3 h; Inert atmosphere of nitrogen;
参考文献
MERCK SERONO S.A.; BOMBRUN, Agnes; QUATTROPANI, Anna; GONZALEZ, Jerome; DORBAIS, Jerome; KNIGHT, Chris; BAKER-GLENN, Charles
Patent: WO2012/4287 A1, 2012 ;
Location in patent: Page/Page column 67-68 ;
WO 2012/004287 A1
反应条件
1: sodium carbonate / 1,3-bis-(diphenylphosphino)propane; palladium diacetate / methanol / 90 °C / Inert atmosphere
2: hydrogenchloride; water / methanol / 0.3 h / 20 °C
View Scheme
参考文献
Millennium Pharmaceuticals, Inc.
Patent: US2011/212969 A1, 2011 ;
US 20110212969 A1
反应条件
1: 4-bromo-3-methyl-benzoic acid methyl ester With tetrakis(triphenylphosphine) palladium(0) in toluene
T=20°C; 1 h;
2: (4-Chlorophenyl)-boronic acid With sodium carbonate; lithium chloride in ethanol; water; toluene
T=20°C; 50 h; Heating / reflux;
参考文献
GLAXO GROUP LIMITED
Patent: WO2004/7493 A1, 2004 ;
Location in patent: Page 28 ;
