3-bromo-6-(6-chloropyridin-3-yloxy)pyridine | 900493-25-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-bromo-6-(6-chloropyridin-3-yloxy)pyridine
• 英文别名: 5-Bromo-2-[(6-chloropyridin-3-yl)oxy]pyridine；5-bromo-2-(6-chloropyridin-3-yl)oxypyridine
• CAS: 900493-25-6
• 化学式: C₁₀H₆BrClN₂O
• 分子量: 285.527
• InChiKey: NIVHVIJNRMAZFT-UHFFFAOYSA-N

物化性质

• 熔点：
  80 °C
• 沸点：
  365.8±37.0 °C(Predicted)
• 密度：
  1.635±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-6-(6-chloropyridin-3-yloxy)pyridine 在 正丁基锂 、 硼酸三异丙酯 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以20%的产率得到6-(6-chloropyridin-3-yloxy)pyridin-3-yl boronic acid
  参考文献：
  名称：

  Novel oxybispyridylboronic acids: synthesis and study of their reactivity in Suzuki-type cross-coupling reactions

  摘要：

  This paper sets forth the synthesis of novel oxybispyridylboronic acids, which are prepared from the corresponding halo-oxybispyridines via halogen-metal exchange using n-butyllithium and treatment with triisopropylborate. A range of efficient cross-coupling reactions of these novel boronic acids with selected aryl halides is described. This strategy produces novel pyridylethers of interest in cholinergic medicinal chemistry. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.036
• 作为产物：
  描述：

  2,5-二溴吡啶 、 2-氯-5-羟基吡啶 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 以63%的产率得到3-bromo-6-(6-chloropyridin-3-yloxy)pyridine
  参考文献：
  名称：

  Synthesis of novel halo-oxybispyridines, new building blocks in cholinergic medicinal chemistry

  摘要：

  This paper describes a method for the preparation of oxybispyridines bearing several halogens, which could be further transformed into other functional groups thus giving access to libraries with the bis-pyridyl ether moiety as the common structural feature of interest in cholinergic medicinal chemistry. Scope and limitation of the method are outlined. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.002

文献信息

• Synthesis of novel halo-oxybispyridines, new building blocks in cholinergic medicinal chemistry
  作者：Anne Sophie Voisin、Alexandre Bouillon、Jean-Charles Lancelot、Aurélien Lesnard、Sylvain Rault

  DOI：10.1016/j.tet.2006.04.002

  日期：2006.6

  This paper describes a method for the preparation of oxybispyridines bearing several halogens, which could be further transformed into other functional groups thus giving access to libraries with the bis-pyridyl ether moiety as the common structural feature of interest in cholinergic medicinal chemistry. Scope and limitation of the method are outlined. (c) 2006 Elsevier Ltd. All rights reserved.
• Novel oxybispyridylboronic acids: synthesis and study of their reactivity in Suzuki-type cross-coupling reactions
  作者：Anne Sophie Voisin、Alexandre Bouillon、Inmaculada Berenguer、Jean-Charles Lancelot、Aurélien Lesnard、Sylvain Rault

  DOI：10.1016/j.tet.2006.09.036

  日期：2006.12

  This paper sets forth the synthesis of novel oxybispyridylboronic acids, which are prepared from the corresponding halo-oxybispyridines via halogen-metal exchange using n-butyllithium and treatment with triisopropylborate. A range of efficient cross-coupling reactions of these novel boronic acids with selected aryl halides is described. This strategy produces novel pyridylethers of interest in cholinergic medicinal chemistry. (c) 2006 Elsevier Ltd. All rights reserved.