4-chloro-N-(3,4,5-trimethoxyphenyl)pyridin-2-amine | 1337906-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-chloro-N-(3,4,5-trimethoxyphenyl)pyridin-2-amine
• CAS: 1337906-15-6
• 化学式: C₁₄H₁₅ClN₂O₃
• 分子量: 294.738
• InChiKey: VCVJCCFYBCAAKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4-二氯吡啶 、 3,4,5-三甲氧基苯胺 在 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以68%的产率得到4-chloro-N-(3,4,5-trimethoxyphenyl)pyridin-2-amine
  参考文献：
  名称：

  Highly regioselective Buchwald–Hartwig amination at C-2 of 2,4-dichloropyridine enabling a novel approach to 2,4-bisanilinopyridine (BAPyd) libraries

  摘要：

  The highly regioselective Buchwald-Hartwig amination at C-2 of the cheap and readily accessible reagent, 2,4-dichloropyridine with a range of anilines and heterocyclic amines is described. This new methodology is robust and provides a facile access to 4-chloro-N-phenylpyridin-2-amines on 0.25 mol scale. These intermediates undergo a further Buchwald-Hartwig amination at higher temperature to enable rapid exploration of the chemical space at C-4 and to provide a library of 2,4-bisaminopyridines. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.035

文献信息

• Highly Regioselective Palladium-Catalyzed C2-Amination of 2,4-Dichloropyridines: Scope and Limitations
  作者：Rémy Morgentin、Christian Delvare、Patrice Koza

  DOI：10.1055/s-0030-1260080

  日期：2011.8

  The use of palladium(0) enables a highly regioselective C-2 amination of 4,6-dichloronicotinonitrile. Coupling with aminoarenes that are N-acetyl-masked to limit cross-coupling overreaction, leads to 4-chloro-6-anilino nicotinonitrile compounds after deprotection in situ. The scope of these original conditions was evaluated.

  使用零价钯催化剂实现了对4,6-二氯烟腈的高度区域选择性的C-2胺化反应。通过与N-乙酰化保护的氨基芳烃进行偶联，以限制交叉偶联过度反应，然后在原位脱保护后得到4-氯-6-苯胺烟腈化合物。这些原始反应条件的适用范围得到了评估。
• Highly regioselective Buchwald–Hartwig amination at C-2 of 2,4-dichloropyridine enabling a novel approach to 2,4-bisanilinopyridine (BAPyd) libraries
  作者：Rebecca J. Burton、Mandy L. Crowther、Neal J. Fazakerley、Shaun M. Fillery、Barry M. Hayter、Jason G. Kettle、Caroline A. McMillan、Paula Perkins、Peter Robins、Peter M. Smith、Emma J. Williams、Gail L. Wrigley

  DOI：10.1016/j.tetlet.2013.10.035

  日期：2013.12

  The highly regioselective Buchwald-Hartwig amination at C-2 of the cheap and readily accessible reagent, 2,4-dichloropyridine with a range of anilines and heterocyclic amines is described. This new methodology is robust and provides a facile access to 4-chloro-N-phenylpyridin-2-amines on 0.25 mol scale. These intermediates undergo a further Buchwald-Hartwig amination at higher temperature to enable rapid exploration of the chemical space at C-4 and to provide a library of 2,4-bisaminopyridines. (C) 2013 Elsevier Ltd. All rights reserved.