2-bromo-N,N-diethyl-3-methyl-1H-indole-1-carboxamide | 920981-29-9

• 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-bromo-N,N-diethyl-3-methyl-1H-indole-1-carboxamide
• 英文别名: 2-bromo-N,N-diethyl-3-methylindole-1-carboxamide
• CAS: 920981-29-9
• 化学式: C₁₄H₁₇BrN₂O
• 分子量: 309.206
• InChiKey: APUBIQSWEZBXGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-N,N-diethyl-3-methyl-1H-indole-1-carboxamide 、 3-呋喃硼酸 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 作用下， 以 甲醇 为溶剂， 反应 55.0h， 以65%的产率得到N,N-diethyl-2-(furan-3-yl)-3-methyl-1H-indole-1-carboxamide
  参考文献：
  名称：

  Anionic Indole N-Carbamoyl N → C Translocation. A Directed remote Metalation Route to 2-Aryl- and 2-Heteroarylindoles. Synthesis of Benz[a]carbazoles and Indeno[1,2-b]indoles

  摘要：

  A new LDA-induced anionic N-C carbamoyl migration of 2-arylindoles (7) is reported. Treatment of N-carbamoylindoles 10 and 13, readily available by direct and ipso-borodesilylative Suzuki-Miyaura cross-coupling routes from 8 and 12, respectively, provides a general route to functionalized 2-arylindoles 11 and 14, respectively (Tables 1 and 2). The reaction has been applied to the synthesis of benzo[a]carbazoles 16 and indeno[1,2-b]indoles 18, and its intramolecularity has been established by a crossover experiment (Scheme 4).

  DOI：

  10.1021/ol800307g
• 作为产物：
  描述：

  N,N-diethyl-3-methyl-2-(trimethylsilyl)-1H-indole-1-carboxamide 在 pyridinium hydrobromide perbromide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到2-bromo-N,N-diethyl-3-methyl-1H-indole-1-carboxamide
  参考文献：
  名称：

  Anionic Indole N-Carbamoyl N → C Translocation. A Directed remote Metalation Route to 2-Aryl- and 2-Heteroarylindoles. Synthesis of Benz[a]carbazoles and Indeno[1,2-b]indoles

  摘要：

  A new LDA-induced anionic N-C carbamoyl migration of 2-arylindoles (7) is reported. Treatment of N-carbamoylindoles 10 and 13, readily available by direct and ipso-borodesilylative Suzuki-Miyaura cross-coupling routes from 8 and 12, respectively, provides a general route to functionalized 2-arylindoles 11 and 14, respectively (Tables 1 and 2). The reaction has been applied to the synthesis of benzo[a]carbazoles 16 and indeno[1,2-b]indoles 18, and its intramolecularity has been established by a crossover experiment (Scheme 4).

  DOI：

  10.1021/ol800307g

文献信息

• A Mixed Naphthyl-Phenyl Phosphine Ligand Motif for Suzuki, Heck, and Hydrodehalogenation Reactions
  作者：Oleg Demchuk、Victor Snieckus、Bilge Yoruk、Tom Blackburn

  DOI：10.1055/s-2006-951538

  日期：2006.11

  Nap-Phos, representing a new naphthyl-phenyl biaryl-type phosphine ligand class and available by a short synthesis (4 steps, 71% overall yield), effectively catalyzes the Suzuki-Miyaura (including highly hindered cases), hydrodehalogenation, and Heck reactions.

  Nap-Phos代表着一种新型萘基-苯基双芳基膦配体，可通过短合成路线（4步，总产率71%）制备，并能有效催化铃木-宫浦反应（包括高度受阻的情况）、氢去卤反应和赫克反应。
• Urea-accelerated Iridium-catalyzed 2-Position-selective C–H Borylation of Indole Derivatives
  作者：Jie Wang、Takeru Torigoe、Yoichiro Kuninobu

  DOI：10.1246/cl.200939

  日期：2021.4.5

  scale, and were dramatically improved by the addition of a urea derivative catalyst. The introduced boryl group was converted to chloro, bromo, and phenyl groups without isolation of the borylated intermediate. Preliminary results indicated the importance of hydrogen bonding between the substrate and the urea additive.

  我们通过修饰联吡啶型配体的结构开发了铱催化的吲哚衍生物的2位选择性C–H硼氢化。甚至在克规模上，收率从好到坏不等，并且通过添加脲衍生物催化剂而大大提高了收率。引入的硼基被转化为氯，溴和苯基，而没有分离出硼化的中间体。初步结果表明，底物与尿素添加剂之间氢键的重要性。