ethyl 3-(4-bromophenyl)-1H-indole-2-carboxylate | 1246775-33-6

• 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: ethyl 3-(4-bromophenyl)-1H-indole-2-carboxylate
• CAS: 1246775-33-6
• 化学式: C₁₇H₁₄BrNO₂
• 分子量: 344.208
• InChiKey: DAQHICYILBEDNO-UHFFFAOYSA-N

物化性质

• 熔点：
  165.0-165.5 °C
• 沸点：
  516.2±45.0 °C(predicted)
• 密度：
  1.447±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 3-(4-bromophenyl)-1H-indole-2-carboxylate 、 4-叔丁基苯硼酸 在 palladium diacetate 、 potassium hydrogencarbonate 、 三(邻甲基苯基)磷 、 sodium hydrogen sulfate 作用下， 以 水 、 异丙醇 、 甲苯 为溶剂， 反应 3.0h， 以82%的产率得到ethyl 3-[4-(1,1-dimethylethyl)phenyl]-1H-indole-2-carboxylate
  参考文献：
  名称：

  Optimization and Scale-Up of a Suzuki−Miyaura Coupling Reaction: Development of an Efficient Palladium Removal Technique

  摘要：

  A ligand-solvent-base screen was performed on a Suzuki-Myaura coupling reaction, and the screening data, followed by a set of focused experiments, helped to optimize reaction conditions. Further work was carried out that centered on reducing the level of residual palladium in the isolated product. Treatment of the reaction mixture with toluene and 20% aqueous NaHSO3 at elevated temperature lowered the palladium content from similar to 8000 ppm to 100 ppm or less. The Suzuki-Miyaura coupling and palladium removal process were demonstrated on 20-L scale, are highly efficient and cost-effective, and require short cycle times.

  DOI：

  10.1021/op800064y
• 作为产物：
  描述：

  (2-硝基-苯基)-丙炔酸乙酯 在 {MoO2Cl2(dmf)2} 、 copper (I) acetate 、 三苯基膦 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 7.0h， 生成 ethyl 3-(4-bromophenyl)-1H-indole-2-carboxylate
  参考文献：
  名称：

  通过铜催化邻硝基苯基取代的炔烃的氢芳基化反应和随后的Cadogan环化反应合成3-芳基吲哚-2-羧酸盐

  摘要：

  已经成功地建立了具有生物重要性的3-芳基吲哚-2-羧酸酯的两步法：在商业上可获得的芳基硼酸存在下，对邻硝基苯基取代的炔酸酯进行铜催化的氢芳基化反应，得到3,3-二芳基丙烯酸酯。然后使用钼催化剂和三苯基膦经改良的Cadogan环化反应转化为吲哚羧酸酯。

  DOI：

  10.1002/adsc.201000858

文献信息

• Synthesis of Substituted Indoles from 2-Azidoacrylates and <i>ortho</i>-Silyl Aryltriflates
  作者：Deng Hong、Zhengbo Chen、Xufeng Lin、Yanguang Wang

  DOI：10.1021/ol101934v

  日期：2010.10.15

  2-Azidoacrylates react with benzynes in the presence of PPh3 and CsF to afford substituted indoles in good yields. The reaction involves the formation of iminophosphorane and benzyne and a subsequent double cyclization/hydrolysis/air-oxidation cascade. This methodology was utilized to synthesize 10H-indolo[1,2-a]indol-10-ones.

  2-叠氮基丙烯酸酯在PPh 3和CsF的存在下与苯炔反应，以高收率提供取代的吲哚。该反应涉及亚氨基磷烷和苯炔的形成以及随后的双环化/水解/空气氧化级联反应。该方法用于合成10 H-吲哚并[1,2-a]吲哚-10-酮。
• Synthesis of 3-Arylindole-2-carboxylates via Copper-Catalyzed Hydroarylation of o-Nitrophenyl-Substituted Alkynoates and Subsequent Cadogan Cyclization
  作者：Yoshihiko Yamamoto、Satoshi Yamada、Hisao Nishiyama

  DOI：10.1002/adsc.201000858

  日期：2011.3.28

  A two‐step route to biologically important 3‐arylindole‐2‐carboxylic esters has been successfully established: o‐nitrophenyl‐substituted alkynoates underwent copper‐catalyzed hydroarylation in the presence of commercially available arylboronic acids to afford 3,3‐diarylacrylates, which were then converted to indolecarboxylates via a modified Cadogan cyclization using a molybdenum catalyst and triphenylphosphine

  已经成功地建立了具有生物重要性的3-芳基吲哚-2-羧酸酯的两步法：在商业上可获得的芳基硼酸存在下，对邻硝基苯基取代的炔酸酯进行铜催化的氢芳基化反应，得到3,3-二芳基丙烯酸酯。然后使用钼催化剂和三苯基膦经改良的Cadogan环化反应转化为吲哚羧酸酯。
• Optimization and Scale-Up of a Suzuki−Miyaura Coupling Reaction: Development of an Efficient Palladium Removal Technique
  作者：Kae M. Bullock、Mark B. Mitchell、Jennifer F. Toczko

  DOI：10.1021/op800064y

  日期：2008.9.19

  A ligand-solvent-base screen was performed on a Suzuki-Myaura coupling reaction, and the screening data, followed by a set of focused experiments, helped to optimize reaction conditions. Further work was carried out that centered on reducing the level of residual palladium in the isolated product. Treatment of the reaction mixture with toluene and 20% aqueous NaHSO3 at elevated temperature lowered the palladium content from similar to 8000 ppm to 100 ppm or less. The Suzuki-Miyaura coupling and palladium removal process were demonstrated on 20-L scale, are highly efficient and cost-effective, and require short cycle times.