tert-butyl 2-(2-(methylthio)-6-(trifluoromethyl)pyrimidin-4-yl)-1H-pyrrole-1-carboxylate | 1251914-12-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: tert-butyl 2-(2-(methylthio)-6-(trifluoromethyl)pyrimidin-4-yl)-1H-pyrrole-1-carboxylate
• 英文别名: Tert-butyl 2-[2-methylsulfanyl-6-(trifluoromethyl)pyrimidin-4-yl]pyrrole-1-carboxylate；tert-butyl 2-[2-methylsulfanyl-6-(trifluoromethyl)pyrimidin-4-yl]pyrrole-1-carboxylate
• CAS: 1251914-12-1
• 化学式: C₁₅H₁₆F₃N₃O₂S
• 分子量: 359.372
• InChiKey: CCRLEROTDPSIRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  82.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-Boc-吡咯-2-硼酸 、 4-氯-2-甲硫基-6-三氟甲基嘧啶 在 potassium phosphate 、 XPhos Pd G2 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以88%的产率得到tert-butyl 2-(2-(methylthio)-6-(trifluoromethyl)pyrimidin-4-yl)-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  A New Palladium Precatalyst Allows for the Fast Suzuki−Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids

  摘要：

  Boronic acids which quickly deboronate under basic conditions, such as polyfluorophenylboronic acid and five-membered 2-heteroaromatic boronic acids, are especially challenging coupling partners for Suzuki-Miyaura reactions. Nevertheless, being able to use these substrates is highly desirable for a number of applications. Having found that monodentate biarylphosphine ligands can promote these coupling processes, we developed a precatalyst that forms the catalytically active species under conditions where boronic acid decomposition is slow. With this precatalyst, Suzuki-Miyaura reactions of a wide range of (hetero)aryl chlorides, bromides, and triflates with polyfluorophenyl, 2-furan, 2-thiophene, and 2-pyrroleboronic acids and their analogues proceed at room temperature or 40 degrees C in short reaction times to give the desired products in excellent yields.

  DOI：

  10.1021/ja1073799

文献信息

• A New Palladium Precatalyst Allows for the Fast Suzuki−Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids
  作者：Tom Kinzel、Yong Zhang、Stephen L. Buchwald

  DOI：10.1021/ja1073799

  日期：2010.10.13

  Boronic acids which quickly deboronate under basic conditions, such as polyfluorophenylboronic acid and five-membered 2-heteroaromatic boronic acids, are especially challenging coupling partners for Suzuki-Miyaura reactions. Nevertheless, being able to use these substrates is highly desirable for a number of applications. Having found that monodentate biarylphosphine ligands can promote these coupling processes, we developed a precatalyst that forms the catalytically active species under conditions where boronic acid decomposition is slow. With this precatalyst, Suzuki-Miyaura reactions of a wide range of (hetero)aryl chlorides, bromides, and triflates with polyfluorophenyl, 2-furan, 2-thiophene, and 2-pyrroleboronic acids and their analogues proceed at room temperature or 40 degrees C in short reaction times to give the desired products in excellent yields.