2-[2-(2-Bromophenyl)imidazo[4,5-b]pyridin-3-yl]ethanamine | 1441931-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[2-(2-Bromophenyl)imidazo[4,5-b]pyridin-3-yl]ethanamine
• CAS: 1441931-38-9
• 化学式: C₁₄H₁₃BrN₄
• 分子量: 317.188
• InChiKey: HCTVDRSNBMMIAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[2-(2-Bromophenyl)imidazo[4,5-b]pyridin-3-yl]ethanamine 在 sodium tetrahydroborate 、 palladium diacetate 、 magnesium sulfate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  Atom-Economical Construction of a Rare 6,7-Dihydropyrido[3′,2′:4,5]imidazo[1,2-d][1,4]benzodiazepine Scaffold

  摘要：

  We have developed a route towards novel 6,7-dihydropyrido[3',2':4,5]imidazo[1,2-d][1,4]benzodiazepines, in five straightforward steps from commercially available 2-bromobenzaldehydes and 3-(2-aminoethyl)imidazo[4,5-b]pyridines we have described previously, with full control over the three elements of diversity. The route appears to be suitable for systematic exploration of structure-activity relationships around this medicinally relevant tetracyclic scaffold.

  DOI：

  10.1055/s-0034-1378558
• 作为产物：
  描述：

  邻溴苯甲醛 在 N-溴代丁二酰亚胺(NBS) 、 palladium diacetate 、 铁粉 、 氯化铵 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 生成 2-[2-(2-Bromophenyl)imidazo[4,5-b]pyridin-3-yl]ethanamine
  参考文献：
  名称：

  Atom-Economical Construction of a Rare 6,7-Dihydropyrido[3′,2′:4,5]imidazo[1,2-d][1,4]benzodiazepine Scaffold

  摘要：

  We have developed a route towards novel 6,7-dihydropyrido[3',2':4,5]imidazo[1,2-d][1,4]benzodiazepines, in five straightforward steps from commercially available 2-bromobenzaldehydes and 3-(2-aminoethyl)imidazo[4,5-b]pyridines we have described previously, with full control over the three elements of diversity. The route appears to be suitable for systematic exploration of structure-activity relationships around this medicinally relevant tetracyclic scaffold.

  DOI：

  10.1055/s-0034-1378558

文献信息

• A simple two-step access to diversely substituted imidazo[4,5-b]pyridines and benzimidazoles from readily available 2-imidazolines
  作者：Prashant Mujumdar、Tanja Grkovic、Mikhail Krasavin

  DOI：10.1016/j.tetlet.2013.04.036

  日期：2013.6

  We discovered a facile rearrangement of N-(hetero)aryl 2-imidazolines into diversely substituted imidazo[4,5-b]pyridines and benzimidazoles, under Bechamp reduction conditions. Combined with the earlier reported protocol for Pd-catalyzed (hetero)arylation of 2-imidazolines, it provides a simple two-step access to a range of compounds based on these medicinally important heterocyclic cores. (C) 2013 Elsevier Ltd. All rights reserved.