4-氨基吲唑作为重要中间体，广泛应用于医药合成领域，尤其在含吲唑结构的药物研发中具有关键作用。
医药
合成路线 1（1. 合成：41748-71-4）
产率：100%
合成条件：With hydrogen In ethanol for 4 h;
实验步骤：参考实施例5：吲唑-4-硼酸酯（70）：路线1 EPO（70）（69）向2-甲基-3-硝基苯胺（2.27g，14.91mmol）的乙酸（60mL）溶液中加入亚硝酸钠（1.13g，1.1当量）在水（5mL）中的溶液。 2小时后，将深红色溶液倒入冰/水中，过滤收集得到的沉淀，得到4-硝基-1H-吲唑（67）（1.98g，81％）。4-硝基-1H-吲唑的混合物将（760mg，4.68mmol），炭载钯（10％，催化剂）和乙醇（30mL）在氢气球下搅拌4小时。然后将反应混合物通过硅藻土过滤，真空除去溶剂，得到1H-吲唑-4-基胺（68）（63lmg，100％）。亚硝酸钠（337mg，4.89mmol）水溶液（2mL）在低于0℃下，将1 H-吲唑-4-基胺（63μl，4.74mmol）在6M盐酸（7.2mL）中的悬浮液滴加到该悬浮液中。搅拌30分钟后，将四氟硼酸钠（724mg）加入到反应混合物中。得到粘性溶液，将其过滤并用水短暂洗涤，得到1H-吲唑-4-重氮四氟硼酸盐（69）（218mg，20％），为深红色固体。用氩气吹扫干燥的MeOH（4mL）5分钟。向其中加入1H-吲唑-4-重氮四氟硼酸盐（218mg，0.94mmol），双频哪醇EPO二硼（239mg，1.0当量）和[1，r-双（二苯基膦基）二茂铁]氯化钯（II） （20毫克）。将反应混合物搅拌5小时，然后通过硅藻土过滤。使用快速色谱法纯化残余物，得到所需标题化合物（70），（117mg）。
参考文献：
- [1] Patent: WO2006/46031, 2006, A1. Location in patent: Page/Page column 31-33 [2] Patent: WO2007/42806, 2007, A1. Location in patent: Page/Page column 32-33 [3] Patent: US2008/76768, 2008, A1. Location in patent: Page/Page column 9 [4] Patent: US2008/76758, 2008, A1. Location in patent: Page/Page column 74 [5] Patent: WO2012/82997, 2012, A1. Location in patent: Page/Page column 78 [6] Patent: US2014/65136, 2014, A1. Location in patent: Paragraph 0184 [7] Patent: WO2007/127183, 2007, A1. Location in patent: Page/Page column 139 [8] Patent: WO2009/146406, 2009, A1. Location in patent: Page/Page column 65 [9] Journal of Medicinal Chemistry, 2002, vol. 45, # 3, p. 740 - 743 [10] Patent: US2015/87600, 2015, A1. Location in patent: Page/Page column [11] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 6025 - 6035 [12] Patent: US6534504, 2003, B1 [13] Patent: US6841563, 2005, B1. Location in patent: Page column 19 [14] Patent: WO2012/101654, 2012, A2. Location in patent: Page/Page column 56 [15] Patent: WO2014/16849, 2014, A2. Location in patent: Page/Page column 112 [16] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 23, p. 6194 - 6205 [17] Patent: WO2017/178377, 2017, A1. Location in patent: Page/Page column 42 [18] Patent: WO2009/42607, 2009, A1. Location in patent: Page/Page column 71; 76 [19] Patent: WO2009/97446, 2009, A1. Location in patent: Page/Page column 69; 72 [20] Patent: WO2012/82997, 2012, A1. Location in patent: Page/Page column 81 [21] Heterocycles, 2006, vol. 68, # 12, p. 2595 - 2605 [22] Chemische Berichte, 1920, vol. 53, p. 1213,1216, 1227 [23] Journal of the Chemical Society, 1955, p. 2412,2419 [24] Patent: US2003/158188, 2003, A1 [25] Patent: US6933311, 2005, B2 [26] Patent: US2009/54425, 2009, A1. Location in patent: Page/Page column 35 [27] Patent: US2005/113576, 2005, A1. Location in patent: Page/Page column 36-37 [28] Patent: WO2013/107405, 2013, A1. Location in patent: Page/Page column 75 [29] Patent: US2004/157849, 2004, A1 [30] Patent: US2004/157849, 2004, A1 [31] Patent: US2004/157849, 2004, A1 [32] Patent: US2004/157849, 2004, A1 [33] Patent: US2004/157849, 2004, A1 [34] Patent: US2004/157849, 2004, A1 [35] Patent: US2004/157849, 2004, A1 [36] Patent: WO2007/132171, 2007, A1. Location in patent: Page/Page column 41-42
