作为医药中间体或活性成分,用于相关药物的合成。
医药
合成路线 1(1. 合成:73225-15-7)
产率:89%
合成条件:With caesium carbonate In N,N-dimethyl-formamide at 100℃; Inert atmosphere
实验步骤:将1-氟-4-硝基苯(10g,70.9mmol),2-甲基-1H-咪唑(5.8g,70.9mmol)和Cs 2 CO 3(34.7g,106.4mmol)在脱气的DMF(200mL)中的混合物洗涤。 在氮气下在100℃下加热过夜。 当TLC表明消耗1-氟-4-硝基苯时,将反应混合物真空浓缩。 将残余物用水(300mL)稀释,形成灰色沉淀,分离,得到2-甲基-1-(4-硝基苯基)-1H-咪唑(12.8g,收率89%)。
参考文献:
- [1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 4, p. 597 - 609 [2] Patent: WO2011/75478, 2011, A1. Location in patent: Page/Page column 53 [3] Patent: WO2009/71888, 2009, A1. Location in patent: Page/Page column 83 [4] Patent: US5298520, 1994, A [5] Journal of Medicinal Chemistry, 1995, vol. 38, # 10, p. 1799 - 1810 [6] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1221 - 1227 [7] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 1729 - 1744 [8] Patent: US5128351, 1992, A [9] Patent: US5077409, 1991, A [10] Patent: EP991638, 2005, B1. Location in patent: Page/Page column 52
合成路线 2(2. 合成:73225-15-7)
产率:80%
合成条件:With C 40 H 34 CuIN 6 O 6 ; sodium hydroxide In dimethyl sulfoxide at 100℃; for 4 h; Sealed tube
实验步骤:通用方法:对于催化反应,催化剂C1(12mg,0.01mmol),咪唑(1.0mmol),芳基卤(1.0mmol),NaOH(80mg,2.0mmol)和二甲基亚砜(DMSO,5mL)是 采取密封管。 将反应混合物在100℃下搅拌4小时,然后冷却至室温。 加入5mL H 2 O后,溶液用乙酸乙酯萃取。 然后将有机层用无水Na 2 SO 4干燥,减压除去溶剂。最后通过硅胶柱色谱法得到N-芳基化产物。
参考文献:
- [1] Organic Letters, 2009, vol. 11, # 15, p. 3294 - 3297 [2] Chemistry - A European Journal, 2009, vol. 15, # 36, p. 8971 - 8974 [3] Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry, 2018, vol. 57A, # 2, p. 181 - 185 [4] Patent: US6020357, 2000, A [5] Patent: EP946508, 2009, B1. Location in patent: Page/Page column 64-65