2-(2-chloro-5-fluorophenylamino)pyridine | 1439922-54-9

• 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: 2-(2-chloro-5-fluorophenylamino)pyridine
• 英文别名: N-(2-chloro-5-fluorophenyl)pyridin-2-amine
• CAS: 1439922-54-9
• 化学式: C₁₁H₈ClFN₂
• 分子量: 222.649
• InChiKey: ZMQULZAXAKBKLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 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：
  24.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-chloro-5-fluorophenylamino)pyridine 在 potassium tert-butylate 、 氨 作用下， 反应 1.5h， 以83%的产率得到7-fluoropyrido[1,2-a]benzimidazole
  参考文献：
  名称：

  Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions

  摘要：

  The photo-stimulated cyclization of 2-(2-halophenylamino)pyridines in liquid ammonia afforded pyrido [1,2-a]benzimidazoles via S(RN)1 mediated C-N bond forming reactions in moderate to excellent yields (58-94%). This general synthetic strategy was also extended to a 2-(2-bromophenylamino)pyrazine to give pyrazino[1,2-a]benzimidazole. Attempts to employ this reaction using N-(2-chlorophenyl)-3-isoquinolinamine, however, resulted in C-C bond formation generating 7H-indolo[2,3-c]isoquinoline. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.087
• 作为产物：
  描述：

  2-氯-5-氟苯胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以86%的产率得到2-(2-chloro-5-fluorophenylamino)pyridine
  参考文献：
  名称：

  Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions

  摘要：

  The photo-stimulated cyclization of 2-(2-halophenylamino)pyridines in liquid ammonia afforded pyrido [1,2-a]benzimidazoles via S(RN)1 mediated C-N bond forming reactions in moderate to excellent yields (58-94%). This general synthetic strategy was also extended to a 2-(2-bromophenylamino)pyrazine to give pyrazino[1,2-a]benzimidazole. Attempts to employ this reaction using N-(2-chlorophenyl)-3-isoquinolinamine, however, resulted in C-C bond formation generating 7H-indolo[2,3-c]isoquinoline. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.087

文献信息

• Synthesis of pyrido[1,2-a]benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions
  作者：Silvia M. Barolo、You Wang、Roberto A. Rossi、Gregory D. Cuny

  DOI：10.1016/j.tet.2013.04.087

  日期：2013.7

  The photo-stimulated cyclization of 2-(2-halophenylamino)pyridines in liquid ammonia afforded pyrido [1,2-a]benzimidazoles via S(RN)1 mediated C-N bond forming reactions in moderate to excellent yields (58-94%). This general synthetic strategy was also extended to a 2-(2-bromophenylamino)pyrazine to give pyrazino[1,2-a]benzimidazole. Attempts to employ this reaction using N-(2-chlorophenyl)-3-isoquinolinamine, however, resulted in C-C bond formation generating 7H-indolo[2,3-c]isoquinoline. (C) 2013 Elsevier Ltd. All rights reserved.