2-bromo-6-(N-methylbenz[d,e]imidazo-2-yl)pyridine | 1269771-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-bromo-6-(N-methylbenz[d,e]imidazo-2-yl)pyridine
• 英文别名: 6-bromo-2-(2'-methyl-2'H-benzoimidazole)pyridine；2-(6-bromopyridin-2-yl)-1 methyl-1H-benzimidazole；2-(6-bromopyridin-2-yl)-1-methyl-1H-benzimidazole；2-(6-bromopyridin-2-yl)-1-methylbenzimidazole
• CAS: 1269771-41-6
• 化学式: C₁₃H₁₀BrN₃
• 分子量: 288.147
• InChiKey: MCLSLHJXRLPASP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-6-(N-methylbenz[d,e]imidazo-2-yl)pyridine 在 copper(I) oxide 、 正丁基锂 、 氨 、 三乙胺 作用下， 以 正己烷 、 乙二醇 、 甲苯 为溶剂， -78.0~110.0 ℃ 、1.01 MPa 条件下， 反应 24.0h， 生成 6-(N-di-tert-butylphosphino)-2-(2'-methyl-2'H-benzoimidazole)aminepyridine
  参考文献：
  名称：

  Synthesis of mixed-ligand cobalt complexes and their applications in high cis-1,4-selective butadiene polymerization

  摘要：

  Incomplete oxidation of (N-di-tert-butylphosphino)-6-(2-methyl-2'H-benzoimidazole)-2-aminepyridine dichlorocobalt ((PNCoCl2)-Co-3) in DMF results in a unique co-crystal I formed with three parts including DMF, unit A and unit B complex with Co1 and Co2, respectively (PN3 ligand in unit A: (N-di-tertbutylphosphino)-6-(2'-methyl-2'H-benzoimidazole)-2-aminepyridine, and O=PN3 ligand in unit B: (N-di-tert-butylphosphinoxide)-6-(2'-methyl-2'H-benzoimidazole)-2-aminepyridine), with 1:1:1 molar ratio. Co1 and Co2 complexes both display a five-coordinated distorted-square-pyramidal geometry around the metal center. The Co1 center is coordinated with PN3 ligand via two N atoms from pyridine, benzoimidazole moiety as well as one P atom, and the Co2 center is coordinated with the oxidized ligand O=PN3 via two N atoms from pyridine, benzoimidazole moiety as well as one O atom from DMF molecule, while the oxidized phosphine moiety (O=P) being excluded from the coordination sphere. Activated with AlEt2Cl, the co-crystallized complexes I are able to actively convert butadiene to polybutadiene, affording cis-1,4 polybutadiene with cis-1,4 unit up to 95.5-97.8% and number average molecular weight of cal. 10(5) g/mol. The high cis-1,4 selectivity and monomodal GPC curve of resultant polymer imply that the identical active species generated from two distinctive cobalt centers. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.07.033
• 作为产物：
  描述：

  6-溴-2-吡啶羧酸 在 potassium hydroxide 作用下， 反应 0.08h， 生成 2-bromo-6-(N-methylbenz[d,e]imidazo-2-yl)pyridine
  参考文献：
  名称：

  Synthesis of mixed-ligand cobalt complexes and their applications in high cis-1,4-selective butadiene polymerization

  摘要：

  Incomplete oxidation of (N-di-tert-butylphosphino)-6-(2-methyl-2'H-benzoimidazole)-2-aminepyridine dichlorocobalt ((PNCoCl2)-Co-3) in DMF results in a unique co-crystal I formed with three parts including DMF, unit A and unit B complex with Co1 and Co2, respectively (PN3 ligand in unit A: (N-di-tertbutylphosphino)-6-(2'-methyl-2'H-benzoimidazole)-2-aminepyridine, and O=PN3 ligand in unit B: (N-di-tert-butylphosphinoxide)-6-(2'-methyl-2'H-benzoimidazole)-2-aminepyridine), with 1:1:1 molar ratio. Co1 and Co2 complexes both display a five-coordinated distorted-square-pyramidal geometry around the metal center. The Co1 center is coordinated with PN3 ligand via two N atoms from pyridine, benzoimidazole moiety as well as one P atom, and the Co2 center is coordinated with the oxidized ligand O=PN3 via two N atoms from pyridine, benzoimidazole moiety as well as one O atom from DMF molecule, while the oxidized phosphine moiety (O=P) being excluded from the coordination sphere. Activated with AlEt2Cl, the co-crystallized complexes I are able to actively convert butadiene to polybutadiene, affording cis-1,4 polybutadiene with cis-1,4 unit up to 95.5-97.8% and number average molecular weight of cal. 10(5) g/mol. The high cis-1,4 selectivity and monomodal GPC curve of resultant polymer imply that the identical active species generated from two distinctive cobalt centers. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.07.033

文献信息

• Synthesis of new pyrrole–pyridine-based ligands using an in situ Suzuki coupling method
  作者：Matthias Böttger、Björn Wiegmann、Steffen Schaumburg、Peter G Jones、Wolfgang Kowalsky、Hans-Hermann Johannes

  DOI：10.3762/bjoc.8.116

  日期：——

  The compounds 6-(pyrrol-2-yl)-2,2‘-bipyridine, 2-(pyrrol-2-yl)-1,10-phenanthroline and 2-(2-(N-methylbenz[d,e]imidazole)-6-(pyrrol-2-yl)-pyridine were synthesized by using an in situ generated boronic acid for the Suzuki coupling. Crystals of the products could be grown and exhibited interesting structures by X-ray analysis, one of them showing a chain-like network with the adjacent molecules linked to each other via intermolecular N–H^…N hydrogen bonds.

  化合物6-(吡咯-2-基)-2,2'-联吡啉，2-(吡咯-2-基)-1,10-邻菲啰啉和2-(2-(N-甲基苯并[d,e]咪唑)-6-(吡咯-2-基)-吡啉是通过使用原位生成的硼酸进行铃木偶联合成的。通过X射线分析可以生长出产物的晶体，并展示出有趣的结构，其中之一显示出链状网络，相邻分子通过分子间N–H^…N氢键相互连接。
• BENZIMIDAZOLE DERIVATIVES
  申请人：Nair Sajiv Krishnan

  公开号：US20120157471A1

  公开（公告）日：2012-06-21

  The present invention relates to a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein R 1A , R 1B , R 1C , R 2 , R 3 , R 4 , R 5 , R A , R B , R C and X are as defined herein. These novel benzimidazole derivatives are useful in therapy, in particular for treating diseases or conditions mediated by SMO, including the treatment of abnormal cell growth, such as cancer, in mammals. This invention also relates to a method of using such compounds in the treatment of abnormal cell growth in mammals, especially humans, and to pharmaceutical compositions containing such compounds.

  本发明涉及一种式子(I)的化合物或其药学上可接受的盐，其中R1A、R1B、R1C、R2、R3、R4、R5、RA、RB、RC和X如本文所定义。这些新颖的苯并咪唑衍生物在治疗中有用，特别是用于治疗由SMO介导的疾病或病况，包括哺乳动物中的异常细胞生长，如癌症。本发明还涉及使用这些化合物治疗哺乳动物中的异常细胞生长，特别是人类，并涉及含有这些化合物的药物组成物的方法。
• [EN] BENZIMIDAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS DE BENZIMIDAZOLE
  申请人：PFIZER

  公开号：WO2011027249A3

  公开（公告）日：2011-09-01
• Synthesis of mixed-ligand cobalt complexes and their applications in high cis-1,4-selective butadiene polymerization
  作者：Wen Liu、Weijing Pan、Peng Wang、Wei Li、Jingshan Mu、Gengsheng Weng、Xiaoyu Jia、Dirong Gong、Kuo-Wei Huang

  DOI：10.1016/j.ica.2015.07.033

  日期：2015.9

  Incomplete oxidation of (N-di-tert-butylphosphino)-6-(2-methyl-2'H-benzoimidazole)-2-aminepyridine dichlorocobalt ((PNCoCl2)-Co-3) in DMF results in a unique co-crystal I formed with three parts including DMF, unit A and unit B complex with Co1 and Co2, respectively (PN3 ligand in unit A: (N-di-tertbutylphosphino)-6-(2'-methyl-2'H-benzoimidazole)-2-aminepyridine, and O=PN3 ligand in unit B: (N-di-tert-butylphosphinoxide)-6-(2'-methyl-2'H-benzoimidazole)-2-aminepyridine), with 1:1:1 molar ratio. Co1 and Co2 complexes both display a five-coordinated distorted-square-pyramidal geometry around the metal center. The Co1 center is coordinated with PN3 ligand via two N atoms from pyridine, benzoimidazole moiety as well as one P atom, and the Co2 center is coordinated with the oxidized ligand O=PN3 via two N atoms from pyridine, benzoimidazole moiety as well as one O atom from DMF molecule, while the oxidized phosphine moiety (O=P) being excluded from the coordination sphere. Activated with AlEt2Cl, the co-crystallized complexes I are able to actively convert butadiene to polybutadiene, affording cis-1,4 polybutadiene with cis-1,4 unit up to 95.5-97.8% and number average molecular weight of cal. 10(5) g/mol. The high cis-1,4 selectivity and monomodal GPC curve of resultant polymer imply that the identical active species generated from two distinctive cobalt centers. (C) 2015 Elsevier B.V. All rights reserved.