2-MIDA boronate-N,N,3-trimethyl-1H-indole-1-carboxamide | 1414351-27-1

• 英文名称: 2-MIDA boronate-N,N,3-trimethyl-1H-indole-1-carboxamide
• CAS: 1414351-27-1
• 化学式: C₁₇H₂₀BN₃O₅
• 分子量: 357.174
• InChiKey: LQTVOGZTMDOCMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  溴苯 、 2-MIDA boronate-N,N,3-trimethyl-1H-indole-1-carboxamide 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 palladium diacetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以59%的产率得到N,N,3-trimethyl-2-phenyl-1H-indole-1-carboxamide
  参考文献：
  名称：

  Mild Rh(III)-Catalyzed C–H Activation and Annulation with Alkyne MIDA Boronates: Short, Efficient Synthesis of Heterocyclic Boronic Acid Derivatives

  摘要：

  Taking advantage of Rh(III)-catalyzed C-H activation reactions, we have developed a mild, short, and efficient method for the synthesis of bench-stable 3-isoquinolone MIDA boronates. The reaction is practical and scalable. The product formed has been applied in the Suzuki-Miyaura reaction with high efficiency. This strategy has also been successfully expanded to the synthesis of MIDA boronate functionalized heterocycles such as isoquinoline, pyrrole, and indole.

  DOI：

  10.1021/ja310153v
• 作为产物：
  描述：

  6-methyl-2-prop-1-ynyl-1,3,6,2-dioxazaborocane-4,8-dione 、 非草隆 在 tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate 、 copper diacetate 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以42%的产率得到2-MIDA boronate-N,N,3-trimethyl-1H-indole-1-carboxamide
  参考文献：
  名称：

  Mild Rh(III)-Catalyzed C–H Activation and Annulation with Alkyne MIDA Boronates: Short, Efficient Synthesis of Heterocyclic Boronic Acid Derivatives

  摘要：

  Taking advantage of Rh(III)-catalyzed C-H activation reactions, we have developed a mild, short, and efficient method for the synthesis of bench-stable 3-isoquinolone MIDA boronates. The reaction is practical and scalable. The product formed has been applied in the Suzuki-Miyaura reaction with high efficiency. This strategy has also been successfully expanded to the synthesis of MIDA boronate functionalized heterocycles such as isoquinoline, pyrrole, and indole.

  DOI：

  10.1021/ja310153v