3-Fluoro-2-iodo-4-methylpyridine | 153035-05-3

• 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-Fluoro-2-iodo-4-methylpyridine
• 英文别名: 2-iodo-3-fluoro-4-methylpyridine
• CAS: 153035-05-3
• 化学式: C₆H₅FIN
• 分子量: 237.015
• InChiKey: ZAFHZEAEWJKQJM-UHFFFAOYSA-N

物化性质

• 沸点：
  229.7±35.0 °C(Predicted)
• 密度：
  1.892±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Fluoro-2-iodo-4-methylpyridine 在 四(三苯基膦)钯 吡啶盐酸盐 、 potassium carbonate 作用下， 反应 24.75h， 生成 4-methyl-δ-carboline
  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
• 作为产物：
  描述：

  3-氟-4-碘吡啶 、 碘甲烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到3-Fluoro-2-iodo-4-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

文献信息

• 一种3-氟-4-甲基吡啶-2-羧酸的合成方法
  申请人：阿里生物新材料（常州）有限公司

  公开号：CN110642781B

  公开（公告）日：2022-03-11

  本发明提出一种3‑氟‑4‑甲基吡啶‑2‑羧酸的合成方法，属于药物化学合成领域。以2‑卤代‑3‑氟‑4‑甲基吡啶为原料，在催化剂和碱的作用下，通过插羰偶联、水解反应得到目标产物3‑氟‑4‑甲基吡啶‑2‑羧酸。本方法反应步骤短、合成操作简单，所得到的产物收率较高。