2-[(4-methoxyphenyl)ethynyl]-3-(methylthio)pyridine | 1448147-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[(4-methoxyphenyl)ethynyl]-3-(methylthio)pyridine
• 英文别名: 2-[2-(4-Methoxyphenyl)ethynyl]-3-methylsulfanylpyridine；2-[2-(4-methoxyphenyl)ethynyl]-3-methylsulfanylpyridine
• CAS: 1448147-14-5
• 化学式: C₁₅H₁₃NOS
• 分子量: 255.34
• InChiKey: JBXYDMOYFKMQOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(4-methoxyphenyl)ethynyl]-3-(methylthio)pyridine 在 碘 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以98%的产率得到2-(4-methoxyphenyl)-3-iodothieno[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 2-[(4-methoxyphenyl)ethynyl]-3-(methylthio)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

文献信息

• 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
  作者：Maria-João Queiroz、Agathe Begouin、Daniela Peixoto

  DOI：10.1055/s-0033-1338442

  日期：——

  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.