化学合成。
化学合成
合成路线 1(1. 合成:20870-79-5)
产率:98%
合成条件:at -15℃; for 0.50 h;
实验步骤:5-硝基 - 羟吲哚的制备在-15℃下向羟吲哚(26g)在100mL浓硫酸中的溶液中滴加发烟硝酸(8.4mL)。 小心注意将反应温度保持在-15℃。加完后,将反应物搅拌30分钟,然后倒入冰水中。 形成黄色沉淀,通过过滤分离,得到34克(98%)5-硝基羟吲哚。
参考文献:
- [1] Patent: US2005/256145, 2005, A1. Location in patent: Page/Page column 43 [2] Patent: US2005/256144, 2005, A1. Location in patent: Page/Page column 19 [3] Patent: US2010/75952, 2010, A1. Location in patent: Page/Page column 64 [4] Patent: EP2157093, 2010, A1. Location in patent: Page/Page column 61-62 [5] Patent: US6878733, 2005, B1. Location in patent: Page/Page column 169 [6] Patent: US6350754, 2002, B2. Location in patent: Page column 20 [7] Patent: US2017/165166, 2017, A1. Location in patent: Paragraph 0224; 0225; 0226; 0227; 0228; 0229 [8] Synthetic Communications, 2008, vol. 38, # 17, p. 3017 - 3022 [9] Letters in Organic Chemistry, 2011, vol. 8, # 7, p. 526 - 530 [10] Patent: US6265411, 2001, B1 [11] Patent: WO2015/92118, 2015, A1. Location in patent: Page/Page column 26 [12] Patent: WO2018/109650, 2018, A1. Location in patent: Page/Page column 27 [13] Archiv der Pharmazie, 2015, vol. 348, # 10, p. 715 - 729 [14] Zhurnal Obshchei Khimii, 1956, vol. 26, p. 2019,2023, 2024; engl. Ausg. S. 2251, 2254, 2255 [15] Journal of the American Chemical Society, 1945, vol. 67, p. 500 [16] Patent: US2003/100555, 2003, A1 [17] Patent: US2002/183364, 2002, A1 [18] Patent: US6316635, 2001, B1 [19] Patent: US2003/69421, 2003, A1 [20] Patent: US2003/216410, 2003, A1 [21] Patent: US6051593, 2000, A [22] Patent: US2002/156292, 2002, A1 [23] Patent: US6486185, 2002, B1 [24] Patent: US6114371, 2000, A [25] Patent: US6147106, 2000, A [26] Patent: US6846839, 2005, B1 [27] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7349 - 7353 [28] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 4979 - 4985 [29] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7440 - 7443 [30] MedChemComm, 2014, vol. 5, # 5, p. 655 - 658 [31] Patent: US4118561, 1978, A
合成路线 2(2. 合成:20870-79-5)
产率:81%
合成条件:With 1-fluoro-1,2-phenyliodohydrin-3-(1H)-one In 1,4-dioxane; water at 140℃; for 5 h;
实验步骤:在室温下向0.4mL反应管中加入0.4mL 1,4-二恶烷。再加2mL水,搅拌并混合。称取1-氟-1,2-苯基碘醇-3-(1H) - 酮(175mg, 将0.66mmol)加入到反应管中并搅拌1分钟。将反应管置于140℃油浴中,加入5-硝基吲哚(97mg,0.6mmol),加入内置冷凝器并进行反应 在140℃的油浴中保持5小时.TLC点板显示原料反应完成,将反应管从油浴中取出,冷却至室温,并通过加入10mL饱和碳酸氢钠淬灭。 用乙酸乙酯(20mL)萃取。蒸汽浓缩有机层,柱色谱法得到粉末状固体5-硝基取代的2-茚满酮86mg,收率81%。
参考文献:
- [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 12, p. 1437 - 1442 [2] Patent: CN108129377, 2018, A. Location in patent: Paragraph 0042-0043 [3] International Journal of Chemical Kinetics, 1996, vol. 28, # 4, p. 265 - 274 [4] Tetrahedron Letters, 1987, vol. 28, # 35, p. 4027 - 4030