N-[5-(benzo[b]thiophen-3-yl)pyridin-2-yl]pyridinium aminide | 1224592-57-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: N-[5-(benzo[b]thiophen-3-yl)pyridin-2-yl]pyridinium aminide
• CAS: 1224592-57-7
• 化学式: C₁₈H₁₃N₃S
• 分子量: 303.387
• InChiKey: WZEZFPJVLSHQRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
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• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  N-[5-(benzo[b]thiophen-3-yl)pyridin-2-yl]pyridinium aminide 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到N-[5-(benzo[b]thiophen-3-yl)-3-bromopyridin-2-yl]pyridinium aminide
  参考文献：
  名称：

  Pd-catalyzed reactions on pyridinium N-heteroarylaminides. Step-by-step synthesis of 3,5-unsymmetrically disubstituted 2-aminopyridines

  摘要：

  Suzuki-Miyaura cross-coupling processes on N-pyridinium bromoazinyl aminides allow access to 3,5-disubstituted N-alkyl-2-aminopyridines The synthetic pathway involves a regioselective brommation of pyridinum N-(pyridin-2-yl)aminide and a subsequent reaction with boronic acids to afford monosubstituted aminides in good yields An additional brommation in the 5-position of the pyridine ring followed by a coupling reaction gives pyridinium N-(3,5-diarylpyridin-2-yl)aminides Finally, a regioselective alkylation on the exo-nitrogen and reduction of the N-N bond yields highly substituted 2-aminopyridines (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.02.036
• 作为产物：
  描述：

  苯并噻吩-3-硼酸 、 pyridinium N-(5'-bromopyridin-2'-yl)aminide 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 24.0h， 以82%的产率得到N-[5-(benzo[b]thiophen-3-yl)pyridin-2-yl]pyridinium aminide
  参考文献：
  名称：

  Pd-catalyzed reactions on pyridinium N-heteroarylaminides. Step-by-step synthesis of 3,5-unsymmetrically disubstituted 2-aminopyridines

  摘要：

  Suzuki-Miyaura cross-coupling processes on N-pyridinium bromoazinyl aminides allow access to 3,5-disubstituted N-alkyl-2-aminopyridines The synthetic pathway involves a regioselective brommation of pyridinum N-(pyridin-2-yl)aminide and a subsequent reaction with boronic acids to afford monosubstituted aminides in good yields An additional brommation in the 5-position of the pyridine ring followed by a coupling reaction gives pyridinium N-(3,5-diarylpyridin-2-yl)aminides Finally, a regioselective alkylation on the exo-nitrogen and reduction of the N-N bond yields highly substituted 2-aminopyridines (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.02.036

文献信息

• Pd-catalyzed reactions on pyridinium N-heteroarylaminides. Step-by-step synthesis of 3,5-unsymmetrically disubstituted 2-aminopyridines
  作者：Marta Córdoba、Rafael R. Castillo、M. Luisa Izquierdo、Julio Alvarez-Builla

  DOI：10.1016/j.tet.2010.02.036

  日期：2010.4

  Suzuki-Miyaura cross-coupling processes on N-pyridinium bromoazinyl aminides allow access to 3,5-disubstituted N-alkyl-2-aminopyridines The synthetic pathway involves a regioselective brommation of pyridinum N-(pyridin-2-yl)aminide and a subsequent reaction with boronic acids to afford monosubstituted aminides in good yields An additional brommation in the 5-position of the pyridine ring followed by a coupling reaction gives pyridinium N-(3,5-diarylpyridin-2-yl)aminides Finally, a regioselective alkylation on the exo-nitrogen and reduction of the N-N bond yields highly substituted 2-aminopyridines (C) 2010 Elsevier Ltd All rights reserved