3-bromo-5-(4-methylthiophenyl)-2(1H)-pyridinone | 1443542-91-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-bromo-5-(4-methylthiophenyl)-2(1H)-pyridinone
• 英文别名: 3-bromo-5-(4-methylsulfanylphenyl)-1H-pyridin-2-one
• CAS: 1443542-91-3
• 化学式: C₁₂H₁₀BrNOS
• 分子量: 296.188
• InChiKey: LRYJUHUACJEPSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲硫基苯硼酸 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 甲酸 、 硫酸 、 platinum on carbon 、 potassium carbonate 、 三乙胺 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 17.0h， 生成 3-bromo-5-(4-methylthiophenyl)-2(1H)-pyridinone
  参考文献：
  名称：

  A facile synthesis of 3,5-halo and aryl 1H-pyridin-2-ones from pyridinium N-(pyridin-2-yl)aminide

  摘要：

  The synthesis of halogenated and arylated 1H-pyridin-2-ones starting from pyridinium N-(pyridin-2-yl)aminides is described. The synthetic pathway involves the reaction of pyridinium N-(5-bromopyridin-2-yl)aminide, N-(3-bromo-5-chloropyridin-2-yl)aminide or N-(3,5-dibromopyridin-2-yl)aminide with different boronic acids to afford monosubstituted and disubstituted aminides in good yields. An additional bromination in the 3-position of N-(5-arylpyridin-2-yl)aminides was performed. Finally, reduction of the N-N bond followed by the reaction of the corresponding 2-aminopyridines with sodium nitrite/sulfuric acid in water yields 3,5-disubstituted 1H-pyridin-2-ones in good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.065

文献信息

• A facile synthesis of 3,5-halo and aryl 1H-pyridin-2-ones from pyridinium N-(pyridin-2-yl)aminide
  作者：Fabiana Filace、David Sucunza、M. Luisa Izquierdo、Carolina Burgos、Julio Alvarez-Builla

  DOI：10.1016/j.tet.2013.05.065

  日期：2013.7

  The synthesis of halogenated and arylated 1H-pyridin-2-ones starting from pyridinium N-(pyridin-2-yl)aminides is described. The synthetic pathway involves the reaction of pyridinium N-(5-bromopyridin-2-yl)aminide, N-(3-bromo-5-chloropyridin-2-yl)aminide or N-(3,5-dibromopyridin-2-yl)aminide with different boronic acids to afford monosubstituted and disubstituted aminides in good yields. An additional bromination in the 3-position of N-(5-arylpyridin-2-yl)aminides was performed. Finally, reduction of the N-N bond followed by the reaction of the corresponding 2-aminopyridines with sodium nitrite/sulfuric acid in water yields 3,5-disubstituted 1H-pyridin-2-ones in good yields. (C) 2013 Elsevier Ltd. All rights reserved.