5-methoxy-1-phenyl-1H-indazol-3-ylamine | 1426854-82-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-methoxy-1-phenyl-1H-indazol-3-ylamine
• 英文别名: 5-Methoxy-1-phenylindazol-3-amine；5-methoxy-1-phenylindazol-3-amine
• CAS: 1426854-82-1
• 化学式: C₁₄H₁₃N₃O
• 分子量: 239.277
• InChiKey: MUXPMRUPZACHBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  53.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴-5-甲氧基苯甲腈 、 2-苯基苯并肼 在 potassium carbonate 、 copper(I) bromide 、 L-羟基脯氨酸 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 48.0h， 以75%的产率得到5-methoxy-1-phenyl-1H-indazol-3-ylamine
  参考文献：
  名称：

  Assembly of Substituted 3-Aminoindazoles from 2-Bromobenzonitrile via a CuBr-Catalyzed Coupling/Condensation Cascade Process

  摘要：

  CuBr-catalyzed coupling reaction of 2-halobenzonitriles with hydrazine carboxylic esters and CuBr/4-hydroxy-L-proline-catalyzed coupling reaction of 2-bromobenzonitriles with N'-arylbenzohydrazides proceed smoothly at 60-90 degrees C to provide substituted 3-aminoindazoles through a cascade coupling/condensation (or coupling/deacylation/condensation) process. A wide range of 3-aminoindazoles with substituents at both the 1-position and the phenyl ring part can be prepared from the corresponding coupling partners.

  DOI：

  10.1021/jo400071h

文献信息

• Copper‐Catalyzed <i>N</i> ¹ Coupling of 3‐Aminoindazoles and Related Aminoazoles with Aryl Bromides
  作者：Patrick Cyr、Eve‐Marline Joseph‐Valcin、Patrick Boissarie、Bruno Simoneau、Anne Marinier

  DOI：10.1002/ejoc.202101245

  日期：2022.1.27

  AbstractThe N1‐selective arylation of 3‐aminoindazoles using copper catalysis is herein reported. The reaction uses readily accessible aryl bromides as coupling partners, including those from heterocycles, and allows easy access to a broad variety of substituted 3‐aminoindazoles. The methodology was also examined on other aminoazoles of interest for the pharmaceutical industry.
• Assembly of Substituted 3-Aminoindazoles from 2-Bromobenzonitrile via a CuBr-Catalyzed Coupling/Condensation Cascade Process
  作者：Lanting Xu、Yinsheng Peng、Qiangbiao Pan、Yongwen Jiang、Dawei Ma

  DOI：10.1021/jo400071h

  日期：2013.4.5

  CuBr-catalyzed coupling reaction of 2-halobenzonitriles with hydrazine carboxylic esters and CuBr/4-hydroxy-L-proline-catalyzed coupling reaction of 2-bromobenzonitriles with N'-arylbenzohydrazides proceed smoothly at 60-90 degrees C to provide substituted 3-aminoindazoles through a cascade coupling/condensation (or coupling/deacylation/condensation) process. A wide range of 3-aminoindazoles with substituents at both the 1-position and the phenyl ring part can be prepared from the corresponding coupling partners.