22190-33-6 5-溴吲哚啉

运输信息：冰袋运输。危险描述：非危险化学品，冷藏品；WGK Germany:3，包装类别III，海关编码29339900，存储类别11 - 可燃固体；具有眼部刺激（类别2）、经皮刺激（类别2）、特异性靶器官毒性-一次接触（类别3）的危险性。

5-溴二氢吲哚为吲哚类衍生物，可用作有机中间体，在合成医药、染料等方面有重要应用；其作为吲哚类衍生物，许多苯环上含有取代基的吲哚都具有生理活性。

医药; 染料

路线1：

• 步骤: A）将38g（0.16mol）N-乙酰基-5-溴二氢吲哚，31g浓盐酸和41g乙醇的混合物加入反应烧瓶中并均匀搅拌，得到反应混合物I；B）反应混合物I在78℃，反应4h，原料的色谱监测消失；C）用55g氢氧化钠溶液中和；D）获得有机相J和水相K；E）将有机相J用445g氯仿萃取三次。合并有机层，回收溶剂，得到30.74g 5-溴二氢吲哚，产率98.04％，含量≥99％。
• 条件: With hydrogenchloride In ethanol; water at 78℃; for 4 h; Green chemistry
• 收率: 98.04%
• 参考文献: [1] Patent: CN106432040, 2017, A. Location in patent: Paragraph 0108-0113; 0135-0140; 0162-0167 [2] European Journal of Medicinal Chemistry, 2006, vol. 41, # 1, p. 88 - 100 [3] Tetrahedron Letters, 2004, vol. 45, # 25, p. 4827 - 4830 [4] Patent: CN106966950, 2017, A. Location in patent: Paragraph 0022 [5] Patent: US2011/98311, 2011, A1 [6] Patent: US2012/309758, 2012, A1 [7] Synlett, 2007, # 15, p. 2405 - 2409 [8] Patent: WO2004/65351, 2004, A1. Location in patent: Page 82 [9] Patent: US2012/309758, 2012, A1. Location in patent: Page/Page column 77 [10] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 0471

路线2：

• 步骤: 实施例28 5-乙烯基二氢吲哚-1-羧酸叔丁酯（BI10）的制备步骤1. 5-溴-二氢吲哚（BI11）；在10分钟内，在20分钟内向5-溴-1H-吲哚（2.5g，12.82mmol）的乙酸（10.0mL）溶液中分批加入NaCNBH₃（2.38g，38.46mmol）。将混合物在室温下搅拌3小时。将反应混合物用水稀释并用乙醚萃取。用饱和NaHCO₃，水和盐水溶液洗涤有机层。将合并的醚层用无水Na₂SO₄干燥，并在减压下浓缩，得到标题化合物，为浅黄色半固体（1.8g，71％）。
• 条件: at 10 - 20℃; for 3.33 h;
• 收率: 71%
• 参考文献: [1] Organic Letters, 2013, vol. 15, # 11, p. 2798 - 2801 [2] Chemical Papers, 2016, vol. 70, # 5, p. 635 - 648 [3] Tetrahedron Letters, 2005, vol. 46, # 12, p. 2071 - 2074 [4] Nucleosides, Nucleotides and Nucleic Acids, 2005, vol. 24, # 8, p. 1147 - 1165 [5] Chemical Communications, 2017, vol. 53, # 66, p. 9262 - 9264 [6] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2462 - 2471 [7] Patent: US2012/329649, 2012, A1. Location in patent: Page/Page column 46 [8] Patent: WO2014/100163, 2014, A1. Location in patent: Page/Page column 85 [9] Patent: US2014/171308, 2014, A1. Location in patent: Paragraph 0412 [10] Patent: WO2014/100206, 2014, A1. Location in patent: Page/Page column 86 [11] Patent: US2014/171312, 2014, A1. Location in patent: Paragraph 0577; 0578 [12] Patent: US9211280, 2015, B2. Location in patent: Page/Page column 85-86 [13] Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12219 - 12223 [14] Angew. Chem., 2016, vol. 128, p. 12407 - 12411,5 [15] Patent: EP3239143, 2017, A2. Location in patent: Paragraph 0288 [16] Patent: WO2005/123748, 2005, A1. Location in patent: Page/Page column 70 [17] Patent: WO2013/166015, 2013, A1. Location in patent: Paragraph 0202; 0203 [18] Patent: WO2013/166013, 2013, A1. Location in patent: Paragraph 0122; 0123; 0124 [19] Organic Letters, 2013, vol. 15, # 22, p. 5662 - 5665 [20] Patent: US2014/171314, 2014, A1. Location in patent: Page/Page column [21] RSC Advances, 2015, vol. 5, # 30, p. 23727 - 23736 [22] Chemistry - A European Journal, 2015, vol. 21, # 14, p. 5370 - 5379 [23] Journal of Organic Chemistry, 2016, vol. 81, # 2, p. 396 - 403 [24] Chemical Communications, 2017, vol. 53, # 82, p. 11368 - 11371 [25] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 2425 - 2437 [26] Organic and Biomolecular Chemistry, 2018, vol. 16, # 32, p. 5889 - 5898 [27] Chemical Communications, 2018, vol. 54, # 20, p. 2494 - 2497

路线3：

• 步骤: 然后将20摩尔5-溴-N-甲酰基二氢吲哚溶于40毫升甲醇中，加入25摩尔氢氧化钾水溶液，加热至60-65度直至反应消失，然后用水淬灭，浓缩，用二氯甲烷萃取。浓缩，结晶，干燥，得到化合物5，即5-溴二氢吲哚；产率80％，产品纯度93％。
• 条件: With water; potassium hydroxide In methanol at 60 - 65℃;
• 收率: 80%
• 参考文献: [1] Patent: CN106966950, 2017, A. Location in patent: Paragraph 0019 [2] Advanced Synthesis and Catalysis, 2015, vol. 357, # 16-17, p. 3529 - 3537