(E)-6-nitro-3-[(2-pyridin-2-yl)vinyl]-1H-indazole | 1800295-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: (E)-6-nitro-3-[(2-pyridin-2-yl)vinyl]-1H-indazole
• 英文别名: (E)-6-Nitro-3-(2-(pyridin-2-yl)vinyl)-1H-indazole；6-nitro-3-[(E)-2-pyridin-2-ylethenyl]-1H-indazole
• CAS: 1800295-32-2
• 化学式: C₁₄H₁₀N₄O₂
• 分子量: 266.259
• InChiKey: LGIJJKHZJBOJGN-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-6-nitro-3-[(2-pyridin-2-yl)vinyl]-1H-indazole 在 甲烷磺酸 、 sodiumsulfide nonahydrate 、 硫酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 15.5h， 生成 (E)-6-iodo-3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
  参考文献：
  名称：

  Effective Laboratory-Scale Preparation of Axitinib by Two CuI-Catalyzed Coupling Reactions

  摘要：

  The discovery and development of an efficient synthesis route to axinitib is reported. The first-generation route researched by Pfizer implemented two Pd-catalyzed coupling reactions as key steps. In this work, the development of Heck-type and C-S coupling reactions catalyzed by CuI is briefly described, using an economial and practical protocol. Aspects of this route, such as selecting optimal ligands, solvent, and other conditions, are discussed in detail. The scale-up experiment was carried out to provide more than 300 g of active pharmaceutical ingredients of axitinib in Form XLI with 99.9% purity in 39% yield. In short, we provide a new choice of synthesis route to axitinib, through two copper-catalyzed coupling reactions with good yield.

  DOI：

  10.1021/acs.oprd.5b00123
• 作为产物：
  描述：

  3-碘-6-硝基吲唑 在 copper(l) iodide 、 1,10-菲罗啉 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 (E)-6-nitro-3-[(2-pyridin-2-yl)vinyl]-1H-indazole
  参考文献：
  名称：

  Effective Laboratory-Scale Preparation of Axitinib by Two CuI-Catalyzed Coupling Reactions

  摘要：

  The discovery and development of an efficient synthesis route to axinitib is reported. The first-generation route researched by Pfizer implemented two Pd-catalyzed coupling reactions as key steps. In this work, the development of Heck-type and C-S coupling reactions catalyzed by CuI is briefly described, using an economial and practical protocol. Aspects of this route, such as selecting optimal ligands, solvent, and other conditions, are discussed in detail. The scale-up experiment was carried out to provide more than 300 g of active pharmaceutical ingredients of axitinib in Form XLI with 99.9% purity in 39% yield. In short, we provide a new choice of synthesis route to axitinib, through two copper-catalyzed coupling reactions with good yield.

  DOI：

  10.1021/acs.oprd.5b00123