3-bromo-5-fluoro-N-(pyridin-2-yl)benzamide | 1333077-73-8

• 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: 3-bromo-5-fluoro-N-(pyridin-2-yl)benzamide
• 英文别名: 3-bromo-5-fluoro-N-pyridin-2-ylbenzamide
• CAS: 1333077-73-8
• 化学式: C₁₂H₈BrFN₂O
• 分子量: 295.111
• InChiKey: AAJHCQDCGRQERM-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-5-fluoro-N-(pyridin-2-yl)benzamide 、 tert-butyl (2R,4S)-2-(tert-butyl)-4-carbamoyl-4-methyloxazolidine-3-carboxylate 在 potassium phosphate 、 copper(l) iodide 、 N,N'-二甲基乙二胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 36.0h， 以48%的产率得到(2R,4S)-tert-butyl 2-(tert-butyl)-4-((3-fluoro-5-(pyridin-2-ylcarbamoyl)phenyl)carbamoyl)-4-methyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis of Cytimidine through a One-Pot Copper-Mediated Amidation Cascade

  摘要：

  A concise synthesis of cytimidine was developed utilizing tandem Cu-mediated N-aryl amidations followed by global deprotection. This sequence exploits a regioselective coupling of an iodobenzamide with a halopyrimidine that allows the union of three fragments in a single synthetic manipulation and will permit the efficient and rapid diversification of the cytimidine core.

  DOI：

  10.1021/ol2018196
• 作为产物：
  描述：

  2-溴吡啶 、 3-溴-5-氟苯甲酰胺 在 potassium phosphate 、 copper(l) iodide 、 1,10-菲罗啉 作用下， 以 1,4-二氧六环 为溶剂， 反应 36.0h， 以57%的产率得到3-bromo-5-fluoro-N-(pyridin-2-yl)benzamide
  参考文献：
  名称：

  Synthesis of Cytimidine through a One-Pot Copper-Mediated Amidation Cascade

  摘要：

  A concise synthesis of cytimidine was developed utilizing tandem Cu-mediated N-aryl amidations followed by global deprotection. This sequence exploits a regioselective coupling of an iodobenzamide with a halopyrimidine that allows the union of three fragments in a single synthetic manipulation and will permit the efficient and rapid diversification of the cytimidine core.

  DOI：

  10.1021/ol2018196

文献信息

• Synthesis of Cytimidine through a One-Pot Copper-Mediated Amidation Cascade
  作者：Catherine M. Serrano、Ryan E. Looper

  DOI：10.1021/ol2018196

  日期：2011.10.7

  A concise synthesis of cytimidine was developed utilizing tandem Cu-mediated N-aryl amidations followed by global deprotection. This sequence exploits a regioselective coupling of an iodobenzamide with a halopyrimidine that allows the union of three fragments in a single synthetic manipulation and will permit the efficient and rapid diversification of the cytimidine core.