3-(methylthio)-2-[(pyridin-3-yl)ethynyl]pyridine | 1448147-17-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(methylthio)-2-[(pyridin-3-yl)ethynyl]pyridine
• 英文别名: 3-Methylsulfanyl-2-(2-pyridin-3-ylethynyl)pyridine
• CAS: 1448147-17-8
• 化学式: C₁₃H₁₀N₂S
• 分子量: 226.302
• InChiKey: MQPKLSZQAWOVNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(methylthio)-2-[(pyridin-3-yl)ethynyl]pyridine 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以90%的产率得到3-iodo-2-(pyridin-3-yl)thieno[3,2-b]pyridine
  参考文献：
  名称：

  Regiocontrolled SNAr Reaction on 2,3-Dihalopyridines with NaSMe To Obtain Bromo(methylthio)pyridines as Key Precursors of 3-Halo-2-(hetero)arylthieno[2,3-b]pyridines and Thieno[3,2-b]pyridines

  摘要：

  The synthesis of 3-halo-2-(hetero) arylthieno[2,3-b]pyridines and 3-halo-2-(hetero) arylthieno[3,2-b]pyridines has been performed through a three-step methodology from 3-bromo-2-chloropyridine or 2-bromo-3-fluoropyridine, respectively. The key step of this methodology is the formation of the required bromo(methylthio)pyridines by a regiocontrolled nucleophilic aromatic substitution (SNAr) with sodium methanethiolate (NaSMe). Then, the Sonogashira coupling with (hetero)arylalkynes followed by a halocyclization with bromine or iodine, afforded the expected 3-halo-2-(hetero)arylthienopyridines.

  DOI：

  10.1055/s-0033-1338442
• 作为产物：
  描述：

  2-溴-3-氟吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-(methylthio)-2-[(pyridin-3-yl)ethynyl]pyridine
  参考文献：
  名称：

  Regiocontrolled SNAr Reaction on 2,3-Dihalopyridines with NaSMe To Obtain Bromo(methylthio)pyridines as Key Precursors of 3-Halo-2-(hetero)arylthieno[2,3-b]pyridines and Thieno[3,2-b]pyridines

  摘要：

  The synthesis of 3-halo-2-(hetero) arylthieno[2,3-b]pyridines and 3-halo-2-(hetero) arylthieno[3,2-b]pyridines has been performed through a three-step methodology from 3-bromo-2-chloropyridine or 2-bromo-3-fluoropyridine, respectively. The key step of this methodology is the formation of the required bromo(methylthio)pyridines by a regiocontrolled nucleophilic aromatic substitution (SNAr) with sodium methanethiolate (NaSMe). Then, the Sonogashira coupling with (hetero)arylalkynes followed by a halocyclization with bromine or iodine, afforded the expected 3-halo-2-(hetero)arylthienopyridines.

  DOI：

  10.1055/s-0033-1338442