3-Azido-2-fluoro-4-iodo-5-methylpyridine | 153034-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-Azido-2-fluoro-4-iodo-5-methylpyridine
• CAS: 153034-97-0
• 化学式: C₆H₄FIN₄
• 分子量: 278.027
• InChiKey: ZDZAZOQNQHXOEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  27.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Azido-2-fluoro-4-iodo-5-methylpyridine 在 乙醇 、 硫化氢 、 sodium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 180.0 ℃ 、810.6 kPa 条件下， 反应 40.0h， 生成 Diethyl-carbamic acid 6-[3-(2,2-dimethyl-propionylamino)-2-fluoro-5-methyl-pyridin-4-yl]-2,3-dimethoxy-phenyl ester
  参考文献：
  名称：

  Metallation in connection with cross-coupling reactions. Coupling of hindered aryls for the synthesis of 4-phenylpyridines as part of Streptonigrin and Lavendamycin analogues

  摘要：

  The synthesis of the C-D ring system of Streptonigrin and Lavendamycin alkaloid analogues by cross-coupling under Suzuki's conditions has been studied. Steric hindrance is the main problem. It has been solved either by using strong bases or working in a sealed tube under pressure.

  DOI：

  10.1016/0022-328x(95)05979-y
• 作为产物：
  描述：

  2-氟-3-碘-5-甲基吡啶 在 对甲苯磺酰叠氮 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到3-Azido-2-fluoro-4-iodo-5-methylpyridine
  参考文献：
  名称：

  First metalation of aryl iodides: directed ortho-lithiation of iodopyridines, halogen-dance, and application to synthesis

  摘要：

  Metalation of iodopyridines was successfully achieved by LDA at low temperature. In many cases, lithiation is ortho directed by the iodo group which subsequently ortho-migrates very fast to give stabilized iodolithiopyridines. This procedure was applied to 2-fluoro-and 2-chloro-3-iodopyridines, 3-fluoro-4-iodopyridine, and 2-chloro-3-fluoro-4-iodopyridine. The resulting lithio intermediates were obtained in high yields before being reacted with electrophiles leading to various polysubstituted pyridines. Some of these iodopyridines were used as key molecules for the synthesis of fused polyaromatic alkaloids. Thus, perlolidine, delta-carbolines, and 2,10-diazaphenanthrenes were readily prepared in few steps taking advantage of the iodo reactivity for heteroring cross-coupling.

  DOI：

  10.1021/jo00079a031