化学合成。
化学合成
合成路线 1（1. 合成：10389-51-2）
产率：95%
合成条件：With sodium t-butanolate In dimethyl sulfoxide at 110℃; for 12 h; Green chemistry
实验步骤：通用方法：在1mL DMSO中加入芳基卤（1.0mmol），仲胺（1mmol），2mmol tBuONa和0.2mol％Pd / Nf-G催化剂，反应在110℃下进行12小时。 通过气相色谱（GC）监测反应进程。 反应完成后，将反应混合物冷却至室温并用乙酸乙酯萃取。 通过简单过滤容易回收催化剂，然后用乙醇洗涤并干燥并保存用于nextruns。 使用己烷：乙酸乙酯作为洗脱液，通过柱色谱法获得纯产物。 保存的催化剂在随后的可再循环性研究中重复使用。 通过气相色谱（GC）测定反应物的转化率。
参考文献：
- [1] Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 1, p. 42 - 49 [2] Applied Organometallic Chemistry, 2013, vol. 27, # 12, p. 704 - 706 [3] RSC Advances, 2014, vol. 4, # 96, p. 53387 - 53396 [4] Tetrahedron Letters, 2015, vol. 56, # 30, p. 4463 - 4467 [5] Tetrahedron Letters, 2016, vol. 57, # 14, p. 1532 - 1536 [6] Advanced Synthesis and Catalysis, 2017, vol. 359, # 16, p. 2832 - 2846 [7] Synlett, 2004, # 10, p. 1747 - 1750 [8] Applied Organometallic Chemistry, 2014, vol. 28, # 11, p. 809 - 813 [9] Green Chemistry, 2018, vol. 20, # 23, p. 5346 - 5357 [10] European Journal of Organic Chemistry, 2010, # 19, p. 3621 - 3630 [11] Green Chemistry, 2010, vol. 12, # 2, p. 276 - 281
合成路线 2（2. 合成：10389-51-2）
产率：99%
合成条件：With C 28 H 29 Cl 2 N 3 OPd; potassium tert -butylate In toluene at 110℃; for 15 h; Schlenk technique; Inert atmosphere
实验步骤：一般程序：向Schlenk询问了所需的芳基氯（0.25mmol），胺（0.30mmol），N-杂环卡宾 - 钯（II）络合物（2mol），KOtBu（1.3当量）和甲苯（0.5mL））。 在N 2下将混合物在110℃下搅拌15小时。 冷却后，蒸发混合物，通过制备型TLC在硅胶板上分离产物。 通过1H NMR光谱鉴定纯化的产物，并且在支持信息中给出它们的分析数据。
参考文献：
- [1] Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 1, p. 42 - 49 [2] Chemistry Letters, 1987, p. 1187 - 1190 [3] Chemistry Letters, 1987, p. 1187 - 1190 [4] Journal of Organic Chemistry, 2004, vol. 69, # 26, p. 9135 - 9142 [5] Chemical Communications, 2011, vol. 47, # 45, p. 12358 - 12360 [6] European Journal of Organic Chemistry, 2015, vol. 2015, # 9, p. 2042 - 2050 [7] Transition Metal Chemistry, 2016, vol. 41, # 5, p. 525 - 529 [8] European Journal of Organic Chemistry, 2010, # 19, p. 3621 - 3630 [9] Chemistry - A European Journal, 2011, vol. 17, # 11, p. 3086 - 3090 [10] Synthetic Communications, 2000, vol. 30, # 24, p. 4479 - 4488 [11] Journal of Organic Chemistry, 2003, vol. 68, # 22, p. 8416 - 8423 [12] Patent: US7385058, 2008, B1. Location in patent: Page/Page column 27-30; 35 [13] Patent: CN108570012, 2018, A. Location in patent: Paragraph 0040; 0042; 0043 [14] Chemistry - A European Journal, 2008, vol. 14, # 8, p. 2443 - 2452 [15] Tetrahedron Letters, 2011, vol. 52, # 41, p. 5220 - 5223 [16] Journal of Organic Chemistry, 2009, vol. 74, # 20, p. 7951 - 7954 [17] European Journal of Organic Chemistry, 2010, # 35, p. 6824 - 6830 [18] RSC Advances, 2014, vol. 4, # 99, p. 55815 - 55826 [19] Journal of the Iranian Chemical Society, 2015, vol. 12, # 11, p. 2057 - 2064 [20] Journal of Organic Chemistry, 2002, vol. 67, # 18, p. 6479 - 6486 [21] Journal of Organic Chemistry, 2008, vol. 73, # 8, p. 3047 - 3062 [22] Applied Organometallic Chemistry, 2014, vol. 28, # 11, p. 809 - 813 [23] Green Chemistry, 2016, vol. 18, # 20, p. 5580 - 5585 [24] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 1036 - 1050 [25] Synthesis, 2009, # 15, p. 2517 - 2522 [26] Chinese Journal of Chemistry, 2014, vol. 32, # 8, p. 685 - 688 [27] Patent: CN108623537, 2018, A. Location in patent: Paragraph 0087; 0088 [28] European Journal of Organic Chemistry, 2015, vol. 2015, # 18, p. 4018 - 4023 [29] European Journal of Medicinal Chemistry, 2014, vol. 86, p. 257 - 269 [30] Medicinal Chemistry, 2016, vol. 12, # 5, p. 489 - 498 [31] Catalysis Letters, 2017, vol. 147, # 6, p. 1371 - 1378 [32] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 7, p. 1515 - 1518 [33] Patent: CN104230845, 2017, B. Location in patent: Paragraph 0389; 0390 [34] Journal of Organometallic Chemistry, 2017, vol. 851, p. 210 - 217 [35] RSC Advances, 2014, vol. 4, # 96, p. 53387 - 53396 [36] Tetrahedron Letters, 2013, vol. 54, # 9, p. 1120 - 1124 [37] Tetrahedron Letters, 2012, vol. 53, # 39, p. 5318 - 5322 [38] Synlett, 2004, # 10, p. 1747 - 1750 [39] Tetrahedron, 2013, vol. 69, # 2, p. 673 - 679 [40] Patent: EP2949647, 2015, A1. Location in patent: Paragraph 0119 [41] Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5553 - 5566 [42] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 174 - 184 [43] European Journal of Organic Chemistry, 2010, # 33, p. 6404 - 6408 [44] Journal of the American Chemical Society, 1946, vol. 68, p. 1296 [45] Journal of the American Chemical Society, 1948, vol. 70, p. 2223,2228 [46] Journal of the American Chemical Society, 1952, vol. 74, p. 2597,2599 [47] Chemical Communications, 2005, # 22, p. 2857 - 2859 [48] Chemistry - A European Journal, 2010, vol. 16, # 35, p. 10735 - 10743 [49] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 593 - 619
合成路线 3（3. 合成：10389-51-2）
产率：98%
合成条件：With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 6 h; Inert atmosphere
实验步骤：一般步骤：将芳基卤化物（1.0mmol），胺（1.5-2.0mmol），PNP-SSS（0.6mol％; 0.023g），K 2 CO 3（2mmol）和DMF（3.0mL）置于装有磁性的25mL烧瓶中 搅拌棒并在氮气下在120℃下加热。 然后通过TLC监测反应，直至检测到芳基卤的消耗。 反应完成后，向反应混合物中加入5mL水和5mL乙酸乙酯。 萃取有机溶液并经无水Na 2 SO 4干燥。 除去有机溶剂后，得到粗产物。 为了进一步纯化，使用色谱技术。
参考文献：
- [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 10, p. 1908 - 1914 [2] Chemistry - A European Journal, 2008, vol. 14, # 8, p. 2443 - 2452 [3] Tetrahedron Letters, 2013, vol. 54, # 9, p. 1120 - 1124 [4] Journal of Organometallic Chemistry, 2017, vol. 851, p. 210 - 217 [5] Tetrahedron Letters, 2004, vol. 45, # 24, p. 4715 - 4718 [6] Applied Organometallic Chemistry, 2013, vol. 27, # 12, p. 704 - 706 [7] Journal of Organic Chemistry, 2003, vol. 68, # 22, p. 8416 - 8423 [8] Patent: US7385058, 2008, B1. Location in patent: Page/Page column 23-26; 34-35 [9] European Journal of Organic Chemistry, 2013, # 20, p. 4233 - 4237 [10] Applied Organometallic Chemistry, 2014, vol. 28, # 11, p. 809 - 813 [11] Advanced Synthesis and Catalysis, 2017, vol. 359, # 16, p. 2832 - 2846 [12] Synlett, 2004, # 10, p. 1747 - 1750 [13] Synthesis, 2003, # 11, p. 1727 - 1731 [14] Journal of Organometallic Chemistry, 2009, vol. 694, # 9-10, p. 1473 - 1481 [15] Tetrahedron Letters, 2003, vol. 44, # 10, p. 2217 - 2220 [16] Synlett, 1999, # 8, p. 1223 - 1226 [17] Applied Organometallic Chemistry, 2018, vol. 32, # 1, [18] Advanced Synthesis and Catalysis, 2008, vol. 350, # 17, p. 2767 - 2777 [19] Chinese Journal of Chemistry, 2014, vol. 32, # 8, p. 685 - 688 [20] European Journal of Medicinal Chemistry, 2016, vol. 124, p. 896 - 905 [21] Journal of Organometallic Chemistry, 2018, vol. 861, p. 125 - 130 [22] Chemical Communications, 2005, # 22, p. 2857 - 2859 [23] Inorganica Chimica Acta, 2010, vol. 363, # 6, p. 1262 - 1268
