methyl 4-bromothieno[2,3-c]pyridine-2-carboxamide | 1009104-16-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: methyl 4-bromothieno[2,3-c]pyridine-2-carboxamide
• 英文别名: 4-bromo-N-methylthieno[2,3-c]pyridine-2-carboxamide
• CAS: 1009104-16-8
• 化学式: C₉H₇BrN₂OS
• 分子量: 271.137
• InChiKey: CUUSDBMQQCMKDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-bromothieno[2,3-c]pyridine-2-carboxamide 、 对氯苯胺 在 tris(dibenzylideneacetone)dipalladium (0) rac-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl 、 18-冠醚-6 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以84%的产率得到methyl 4-(4-chloroanilino)thieno[2,3-c]pyridine-2-carboxamide
  参考文献：
  名称：

  A facile and general synthesis of 2,4‐Di‐ and 2,4,7‐trisubstituted thieno[2,3‐c]pyridines

  摘要：

  Abstractmagnified imageTreatment of 3,5‐dibromo‐ or 3,5‐dichloro‐pyridine‐4‐carboxaldehyde 2 with one equivalent of methyl thioglycolate, followed by exposure to base, provided 4‐bromo‐ or 4‐chloro‐thieno[2,3‐c]pyridine‐2‐carboxylate 4 in good yields. Oxidation of the thieno[2,3‐c]pyridine scaffold such as 7 with mCPBA, followed by treatment with POBr3, introduced a bromine exclusively at the 7‐position of the heterocycle. The 4‐ or 7‐bromide of the thienopyridines readily underwent Suzuki, Stille coupling, and Buchwald amination reactions, to afford 4‐ or 7‐substituted analogs 6 or 11. The 2‐carboxylate of 4b or 12 was smoothly removed through saponification and decarboxylation to furnish 15 or 16. Deprotonation of the thienopyridine at C‐2 position, followed by trapping with trimethyltin chloride, afforded a 2‐stannyl analog, which was readily converted to other C‐2 derivatives via Stille reaction.

  DOI：

  10.1002/jhet.5570450106
• 作为产物：
  描述：

  4-溴噻吩并[2,3-C]吡啶-2-甲醛 、 甲胺 以 甲醇 为溶剂， 反应 6.0h， 以90%的产率得到methyl 4-bromothieno[2,3-c]pyridine-2-carboxamide
  参考文献：
  名称：

  A facile and general synthesis of 2,4‐Di‐ and 2,4,7‐trisubstituted thieno[2,3‐c]pyridines

  摘要：

  Abstractmagnified imageTreatment of 3,5‐dibromo‐ or 3,5‐dichloro‐pyridine‐4‐carboxaldehyde 2 with one equivalent of methyl thioglycolate, followed by exposure to base, provided 4‐bromo‐ or 4‐chloro‐thieno[2,3‐c]pyridine‐2‐carboxylate 4 in good yields. Oxidation of the thieno[2,3‐c]pyridine scaffold such as 7 with mCPBA, followed by treatment with POBr3, introduced a bromine exclusively at the 7‐position of the heterocycle. The 4‐ or 7‐bromide of the thienopyridines readily underwent Suzuki, Stille coupling, and Buchwald amination reactions, to afford 4‐ or 7‐substituted analogs 6 or 11. The 2‐carboxylate of 4b or 12 was smoothly removed through saponification and decarboxylation to furnish 15 or 16. Deprotonation of the thienopyridine at C‐2 position, followed by trapping with trimethyltin chloride, afforded a 2‐stannyl analog, which was readily converted to other C‐2 derivatives via Stille reaction.

  DOI：

  10.1002/jhet.5570450106

文献信息

• A facile and general synthesis of 2,4‐Di‐ and 2,4,7‐trisubstituted thieno[2,3‐<i>c</i>]pyridines
  作者：Gui‐Dong Zhu、Indrani W. Gunawardana、Steven A. Boyd、Laura M. Melcher

  DOI：10.1002/jhet.5570450106

  日期：2008.1

  Abstractmagnified imageTreatment of 3,5‐dibromo‐ or 3,5‐dichloro‐pyridine‐4‐carboxaldehyde 2 with one equivalent of methyl thioglycolate, followed by exposure to base, provided 4‐bromo‐ or 4‐chloro‐thieno[2,3‐c]pyridine‐2‐carboxylate 4 in good yields. Oxidation of the thieno[2,3‐c]pyridine scaffold such as 7 with mCPBA, followed by treatment with POBr3, introduced a bromine exclusively at the 7‐position of the heterocycle. The 4‐ or 7‐bromide of the thienopyridines readily underwent Suzuki, Stille coupling, and Buchwald amination reactions, to afford 4‐ or 7‐substituted analogs 6 or 11. The 2‐carboxylate of 4b or 12 was smoothly removed through saponification and decarboxylation to furnish 15 or 16. Deprotonation of the thienopyridine at C‐2 position, followed by trapping with trimethyltin chloride, afforded a 2‐stannyl analog, which was readily converted to other C‐2 derivatives via Stille reaction.