1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridine | 1365094-40-1

• 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: 1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridine
• 英文别名: 1-[(2,4-Dimethoxyphenyl)methyl]imidazo[4,5-b]pyridine
• CAS: 1365094-40-1
• 化学式: C₁₅H₁₅N₃O₂
• 分子量: 269.303
• InChiKey: KHHBEPISQNZEGY-UHFFFAOYSA-N

物化性质

• 沸点：
  465.5±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridine 在 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 19.0h， 生成 tert-butyl (S)-2-(tert-butoxycarbonylamino)-5-[1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridin-2-ylamino]pentanoate
  参考文献：
  名称：

  Total Synthesis of Pentosidine

  摘要：

  Pentosidine, a biologically important advanced glycation endproduct, has been accessed in a rapid, high-yielding manner. The synthesis was accomplished via a six-step sequence starting with 3-amino-2-chloropyridine and features a palladium-catalyzed tandem cross-coupling/cyclization to construct the imidazo[4,5-b]pyridine core.

  DOI：

  10.1021/ol3021226
• 作为产物：
  描述：

  N-[(2,4-dimethoxyphenyl)methyl]-2-nitropyridin-3-amine 在 palladium on activated charcoal 、 氢气 作用下， 生成 1-(2,4-dimethoxybenzyl)-1H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  咪唑并[4,5-b]吡啶类似物的区域选择性合成中，钯催化的2-卤代脱氮嘌呤与有机三氟硼酸钾盐的铃木交叉偶联。

  摘要：

  在本文中，我们报告了在三卤代脱氮嘌呤的Suzuki交叉偶联反应中有机三氟硼酸钾盐作为亲核有机硼试剂的用途。通过使用该方案以良好至优异的产率合成了区域异构的C-2-取代的咪唑并[4，5- b ]吡啶类似物。芳基和杂芳基三氟硼酸酯容易反应，以高收率得到偶联产物，而三氟硼酸烷基酯则反应性较低。发现乙酸四丁铵的利用在提高交叉偶联过程的反应速率中起重要作用。另外，在硼酸和有机三氟硼酸钾盐之间进行了比较研究。

  DOI：

  10.1071/ch15420

文献信息

• Synthesis of Imidazo[4,5-<i>b</i>]pyridines and Imidazo[4,5-<i>b</i>]pyrazines by Palladium Catalyzed Amidation of 2-Chloro-3-amino-heterocycles
  作者：Adam J. Rosenberg、Jinbo Zhao、Daniel A. Clark

  DOI：10.1021/ol300359s

  日期：2012.4.6

  A facile synthesis of imidazo[4,5-b]pyridines and -pyrazines is described using a Pd-catalyzed amide coupling reaction. This reaction provides quick access to products with substitution at N1 and C2. A model system relevant to the natural product pentosidine has been demonstrated, as well as the total synthesis of the mutagen 1-Me-5-PhIP.

  使用Pd催化的酰胺偶联反应描述了咪唑并[4,5- b ]吡啶和-吡嗪的简便合成方法。通过该反应，可以快速获得在N1和C2处被取代的产物。已经证明了与天然产物戊糖苷有关的模型系统，以及诱变剂1-Me-5-PhIP的全合成。
• Synthesis of 2-amino-imidazo[4,5-b]pyridines
  作者：Adam J. Rosenberg、Theresa M. Williams、Abraham J. Jordan、Daniel A. Clark

  DOI：10.1039/c3ob40413g

  日期：——

  The C2 amination of imidazo[4,5-b]pyridines was accomplished through C2 halogenation followed by substitution (SNAr) with functionalized primary and secondary amines. This regioselective sequence is operationally simple and provides an easy access to derivatives of protected imidazo[4,5-b]pyridines.

  咪唑并[4,5-b]吡啶的 C2 amination 是通过 C2 卤化，然后用官能化的伯胺和仲胺进行取代 (SNAr) 来完成的。这种区域选择性序列操作简单，易于获得受保护的咪唑并[4,5-b]吡啶衍生物。
• An Improved Synthesis of Imidazo[4,5-<i>b</i>]pyridines and Imidazo[4,5-<i>b</i>]pyrazines by Palladium Catalyzed Amidation using Xantphos in a 1,4-Dioxane:<i>tert</i>-Amyl Alcohol Solvent System
  作者：Adam J. Rosenberg、Ijaz Ahmed、Robert J. Wilson、Theresa M. Williams、Lauren Kaminsky、Daniel A. Clark

  DOI：10.1002/adsc.201400465

  日期：2014.11.3

  AbstractHerein an improved protocol for the synthesis of imidazo[4,5‐b]pyridines and imidazo[4,5‐b]pyrazines using a palladium‐catalyzed amidation that utilizes Xantphos as an ancillary phosphine ligand is reported. The use of a binary solvent system comprised of 1,4‐dioxane and tert‐amyl alcohol was crucial in eliminating unwanted by‐products.magnified image
• Palladium-Catalyzed Suzuki Cross-Coupling of 2-Halo-Deazapurines with Potassium Organotrifluoroborate Salts in the Regioselective Synthesis of Imidazo[4,5-b]pyridine Analogues
  作者：Bhaskaran Savitha、Ayyiliath. M. Sajith、M. Nibin Joy、K.K. Abdul Khader、A. Muralidharan、M. Syed Ali Padusha、Yadav D. Bodke

  DOI：10.1071/ch15420

  日期：——

  In this paper, we report the use of potassium organotrifluoroborate salts as nucleophilic organoboron reagents in the Suzuki cross-coupling reactions of 2-halo deazapurines. Regio-isomeric C-2-substituted imidazo[4,5-b]pyridine analogues were synthesized by employing this protocol in good to excellent yields. Whereas aryl and heteroaryl trifluoroborates reacted readily to give the coupled products

  在本文中，我们报告了在三卤代脱氮嘌呤的Suzuki交叉偶联反应中有机三氟硼酸钾盐作为亲核有机硼试剂的用途。通过使用该方案以良好至优异的产率合成了区域异构的C-2-取代的咪唑并[4，5- b ]吡啶类似物。芳基和杂芳基三氟硼酸酯容易反应，以高收率得到偶联产物，而三氟硼酸烷基酯则反应性较低。发现乙酸四丁铵的利用在提高交叉偶联过程的反应速率中起重要作用。另外，在硼酸和有机三氟硼酸钾盐之间进行了比较研究。
• Total Synthesis of Pentosidine
  作者：Adam J. Rosenberg、Daniel A. Clark

  DOI：10.1021/ol3021226

  日期：2012.9.7

  Pentosidine, a biologically important advanced glycation endproduct, has been accessed in a rapid, high-yielding manner. The synthesis was accomplished via a six-step sequence starting with 3-amino-2-chloropyridine and features a palladium-catalyzed tandem cross-coupling/cyclization to construct the imidazo[4,5-b]pyridine core.