1-(3-fluorophenyl)-1H-benzo[d]imidazol-2-amine | 1038303-04-6

• 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: 1-(3-fluorophenyl)-1H-benzo[d]imidazol-2-amine
• 英文别名: 1-(3-Fluorophenyl)benzimidazol-2-amine
• CAS: 1038303-04-6
• 化学式: C₁₃H₁₀FN₃
• mdl: MFCD11202294
• 分子量: 227.241
• InChiKey: MEZXIQCJPYUYPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-fluorophenyl)-1H-benzo[d]imidazol-2-amine 、 3-溴苯基异丙醚 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 2-二叔丁基膦-2′,4′,6′-三异丙基-3,6-二甲氧基-1,1′-联苯 作用下， 以 叔丁醇 为溶剂， 反应 5.0h， 以5%的产率得到1-(3-fluorophenyl)-N-(3-isopropoxyphenyl)-1H-benzo[d]imidazol-2-amine
  参考文献：
  名称：

  Catalyst-Controlled Chemoselective Arylation of 2-Aminobenzimidazoles

  摘要：

  The chemoselective and complementary Pd-and Cu-catalyzed N-arylation of 2-aminobenzimidazoles is described. Selective N-arylation of the amino-group was achieved with a Pd-catalyzed method, while selective N-arylation of azole nitrogen was achieved with a Cu-catalyzed procedure. The utility of these complementary sets of conditions is demonstrated in several two-step, selective syntheses of di-arylated aminoazoles.

  DOI：

  10.1002/anie.201204710
• 作为产物：
  描述：

  2-氨基苯并咪唑 、 间氟碘苯 在 copper(l) iodide 、 8-羟基喹啉 、 caesium carbonate 作用下， 以 叔丁醇 为溶剂， 反应 16.0h， 以84%的产率得到1-(3-fluorophenyl)-1H-benzo[d]imidazol-2-amine
  参考文献：
  名称：

  Catalyst-Controlled Chemoselective Arylation of 2-Aminobenzimidazoles

  摘要：

  The chemoselective and complementary Pd-and Cu-catalyzed N-arylation of 2-aminobenzimidazoles is described. Selective N-arylation of the amino-group was achieved with a Pd-catalyzed method, while selective N-arylation of azole nitrogen was achieved with a Cu-catalyzed procedure. The utility of these complementary sets of conditions is demonstrated in several two-step, selective syntheses of di-arylated aminoazoles.

  DOI：

  10.1002/anie.201204710

文献信息

• Catalyst-Controlled Chemoselective Arylation of 2-Aminobenzimidazoles
  作者：Satoshi Ueda、Stephen L. Buchwald

  DOI：10.1002/anie.201204710

  日期：2012.10.8

  The chemoselective and complementary Pd-and Cu-catalyzed N-arylation of 2-aminobenzimidazoles is described. Selective N-arylation of the amino-group was achieved with a Pd-catalyzed method, while selective N-arylation of azole nitrogen was achieved with a Cu-catalyzed procedure. The utility of these complementary sets of conditions is demonstrated in several two-step, selective syntheses of di-arylated aminoazoles.