4-chloro-N-(4-fluorophenyl)pyridin-2-amine

• 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-(4-fluorophenyl)pyridin-2-amine
• 化学式: C₁₁H₈ClFN₂
• 分子量: 222.649
• InChiKey: LSJJPTJOTRXJPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  24.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-N-(4-fluorophenyl)pyridin-2-amine 、 苄胺 在 (R)-1-[(Sp)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine 、 palladium diacetate 、 sodium t-butanolate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.5h， 以74%的产率得到4-N-benzyl-2-N-(4-fluorophenyl)pyridine-2,4-diamine
  参考文献：
  名称：

  Selective palladium-catalysed amination of 4-chloropyridines with benzylamines using the Josiphos ligand

  摘要：

  A synthetic strategy for the synthesis of a library of 4-N-benzylamino-2-N-phenyl-pyridines is herein described. The approach involves a Pd-assisted cross-coupling of a 4-chloro-N-phenylpyridin-2-amine intermediate with a range of benzylamines. A variety of ligands were screened, the most successful being the Josiphos ligand, which gave the desired products in good to moderate yields. The reactions occur quickly, within 30 mm, with full conversion of the intermediate into the desired product. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.115
• 作为产物：
  描述：

  2,4-二氯吡啶 、 4-氟苯胺 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40%的产率得到4-chloro-N-(4-fluorophenyl)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 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.
• Selective palladium-catalysed amination of 4-chloropyridines with benzylamines using the Josiphos ligand
  作者：Janet L. Hawkins、Clare L. Gregson、Lorraine A. Hassall、Jane L. Holmes

  DOI：10.1016/j.tetlet.2014.09.115

  日期：2014.12

  A synthetic strategy for the synthesis of a library of 4-N-benzylamino-2-N-phenyl-pyridines is herein described. The approach involves a Pd-assisted cross-coupling of a 4-chloro-N-phenylpyridin-2-amine intermediate with a range of benzylamines. A variety of ligands were screened, the most successful being the Josiphos ligand, which gave the desired products in good to moderate yields. The reactions occur quickly, within 30 mm, with full conversion of the intermediate into the desired product. (C) 2014 Elsevier Ltd. All rights reserved.