2-{1-methyl-1H-indol-3-yl}nicotinonitrile | 849116-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-{1-methyl-1H-indol-3-yl}nicotinonitrile
• 英文别名: 3-Pyridinecarbonitrile, 2-(1-methyl-1H-indol-3-yl)-；2-(1-methylindol-3-yl)pyridine-3-carbonitrile
• CAS: 849116-26-3
• 化学式: C₁₅H₁₁N₃
• 分子量: 233.272
• InChiKey: XDEZLMATSAIMEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-甲基吲哚 、 2-氯-3-氰基吡啶 在 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以48%的产率得到2-{1-methyl-1H-indol-3-yl}nicotinonitrile
  参考文献：
  名称：

  A New Synthesis of 2-Substituted Pyridines via Aluminum Chloride Induced Heteroarylation of Arenes and Heteroarenes

  摘要：

  We herein report a new synthesis of 2-(hetero)aryl-substituted pyridines via heteroarylation of arenes/heteroarenes through. AlCl3-induced C-C bond-forming reactions. 2-Halopyridines bearing an electron-withdrawing group were reacted with a number of (hetero)arenes to give 2-aryl/heteroaryl-substituted pyridines in good yields.

  DOI：

  10.1021/jo047944h

文献信息

• Metal‐Free Arylation of Pyridine/Quinoline N‐Oxides with Indoles
  作者：Ryo Tsunokawa、Yukiko Karuo、Atsushi Tarui、Kazuyuki Sato、Takaaki Hosoya、Tomohiro Agou、Kentaro Kawai、Masaaki Omote

  DOI：10.1002/ejoc.202300885

  日期：2023.12.13

  Arylation of pyridines/quinolines to nitrogen-adjacent position was achieved by SNAr type reaction between pyridine/quinoline N-oxides and indoles with the help of Tf2O for the generation of highly electrophilic intermediate. The reaction proceeded in a short reaction time, open-air condition and without the use of any transition metals, affording various coupling products.

  通过吡啶/喹啉 N-氧化物与吲哚之间的 S N Ar 型反应，在 Tf 2 O 的帮助下，将吡啶/喹啉向氮相邻位置芳基化，生成高亲电子中间体。该反应在短反应时间、露天条件下进行，不使用任何过渡金属，得到各种偶联产物。
• A New Synthesis of 2-Substituted Pyridines via Aluminum Chloride Induced Heteroarylation of Arenes and Heteroarenes
  作者：Manojit Pal、Venkateswara Rao Batchu、Indu Dager、Nalivela Kumara Swamy、Srinivas Padakanti

  DOI：10.1021/jo047944h

  日期：2005.3.1

  We herein report a new synthesis of 2-(hetero)aryl-substituted pyridines via heteroarylation of arenes/heteroarenes through. AlCl3-induced C-C bond-forming reactions. 2-Halopyridines bearing an electron-withdrawing group were reacted with a number of (hetero)arenes to give 2-aryl/heteroaryl-substituted pyridines in good yields.