5-methoxy-2-(4-trimethylacetylamidophenyl)indole

• 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: 5-methoxy-2-(4-trimethylacetylamidophenyl)indole
• 英文别名: N-[4-(5-methoxy-1H-indol-2-yl)phenyl]-2,2-dimethylpropanamide
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: OYTFHIHQBMYVDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-甲氧基吲哚 、 N-(4-iodophenyl)pivalamide 在 palladium diacetate cesium acetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 36.0h， 以53%的产率得到5-methoxy-2-(4-trimethylacetylamidophenyl)indole
  参考文献：
  名称：

  Phosphine-Free Palladium-Catalyzed C−H Bond Arylation of Free (N−H)-Indoles and Pyrroles

  摘要：

  This paper describes a phosphine-free palladium-catalyzed method for direct C-arylation of free (N-H)-indoles and pyrroles with iodo- and bromoarene donors. Employing commercially available materials, this new and operationally simple procedure provides a rapid entry to a wide range of C-arylated (N-H)-indoles including derivatives of tryptamine. In the course of this study, a profound halide effect was uncovered, affecting both the efficiency and regioselectivity of indole arylation.

  DOI：

  10.1021/jo061979v

文献信息

• Phosphine-Free Palladium-Catalyzed C−H Bond Arylation of Free (N−H)-Indoles and Pyrroles
  作者：Xiang Wang、Denis V. Gribkov、Dalibor Sames

  DOI：10.1021/jo061979v

  日期：2007.2.1

  This paper describes a phosphine-free palladium-catalyzed method for direct C-arylation of free (N-H)-indoles and pyrroles with iodo- and bromoarene donors. Employing commercially available materials, this new and operationally simple procedure provides a rapid entry to a wide range of C-arylated (N-H)-indoles including derivatives of tryptamine. In the course of this study, a profound halide effect was uncovered, affecting both the efficiency and regioselectivity of indole arylation.