N-(6-methylpyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide | 936090-74-3

• 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: N-(6-methylpyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide
• 英文别名: N-(6-methylpyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide
• CAS: 936090-74-3
• 化学式: C₁₈H₂₂BN₃O₃
• 分子量: 339.202
• InChiKey: RDCSNFYTEBVXHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  73.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(6-methylpyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide 、 2-溴嘧啶 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 生成 N-(6-methylpyridin-2-yl)-4-(pyrimidin-2-yl)picolinamide
  参考文献：
  名称：

  Design and synthesis of novel heterobiaryl amides as metabotropic glutamate receptor subtype 5 antagonists

  摘要：

  A series of heterobiaryl amides was designed and synthesized as novel mGluR5 antagonists. The synthesis using palladium catalyzed Suzuki-Miyaura cross-coupling reactions provided art array of compounds with a range of in vitro activities. In particular, compound 9e, 4( 3,5-difluorophenyl)-N-(6-methylpyridin-1-yl)picolinamide, exhibited nanomolar affinity at the mGluR5 and will serve as a template for future drug design. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.083
• 作为产物：
  描述：

  2-Pyridinecarboxamide, 4-chloro-N-(6-methyl-2-pyridinyl)-, hydrobromide 、 联硼酸频那醇酯 在 palladium diacetate 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 60.0h， 以90%的产率得到N-(6-methylpyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide
  参考文献：
  名称：

  Design and synthesis of novel heterobiaryl amides as metabotropic glutamate receptor subtype 5 antagonists

  摘要：

  A series of heterobiaryl amides was designed and synthesized as novel mGluR5 antagonists. The synthesis using palladium catalyzed Suzuki-Miyaura cross-coupling reactions provided art array of compounds with a range of in vitro activities. In particular, compound 9e, 4( 3,5-difluorophenyl)-N-(6-methylpyridin-1-yl)picolinamide, exhibited nanomolar affinity at the mGluR5 and will serve as a template for future drug design. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.083