6-bromo-2-(4-acetylphenyl)-1H-indole | 1315267-82-3

• 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: 6-bromo-2-(4-acetylphenyl)-1H-indole
• 英文别名: 1-[4-(6-bromo-1H-indol-2-yl)phenyl]ethanone
• CAS: 1315267-82-3
• 化学式: C₁₆H₁₂BrNO
• 分子量: 314.181
• InChiKey: QGXNGXOYNVKZOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  benzyl 5-bromo-2-iodophenylcarbamate 在 copper(l) iodide 、 三(2-呋喃基)膦 、 四丁基氟化铵 、 二异丙胺 、 palladium dichloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.5h， 生成 6-bromo-2-(4-acetylphenyl)-1H-indole
  参考文献：
  名称：

  Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor

  摘要：

  The synthesis of 6-bromo-2-arylindoles starting from readily available 2-iodobenzoic acid is presented. Regioselective bromination of the latter was followed by Curtius rearrangement and trapping of the isocyanate with benzyl alcohol led to the benzyl carbamate of 2-iodo-5-bromoaniline. Chemoselective Sonogashira coupling of this compound with arylacetylenes followed by TBAF induced 5-endo-dig cyclization gave the desired bromo indoles. The method allows selective introduction of a bromine atom at the indole C-6 position. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.040

文献信息

• Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor
  作者：Ismael Valois-Escamilla、Alejandro Alvarez-Hernandez、Luis Felipe Rangel-Ramos、Oscar Rodolfo Suárez-Castillo、Francisco Ayala-Mata、Gerardo Zepeda-Vallejo

  DOI：10.1016/j.tetlet.2011.05.040

  日期：2011.7

  The synthesis of 6-bromo-2-arylindoles starting from readily available 2-iodobenzoic acid is presented. Regioselective bromination of the latter was followed by Curtius rearrangement and trapping of the isocyanate with benzyl alcohol led to the benzyl carbamate of 2-iodo-5-bromoaniline. Chemoselective Sonogashira coupling of this compound with arylacetylenes followed by TBAF induced 5-endo-dig cyclization gave the desired bromo indoles. The method allows selective introduction of a bromine atom at the indole C-6 position. (C) 2011 Elsevier Ltd. All rights reserved.