2-(2-chlorophenyl)pyrazolo[1,5-a]pyridine | 1206884-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-chlorophenyl)pyrazolo[1,5-a]pyridine
• 英文别名: 2-(2-Chlorophenyl)pyrazolo[1,5-a]pyridine
• CAS: 1206884-53-8
• 化学式: C₁₃H₉ClN₂
• 分子量: 228.681
• InChiKey: CZGZHJUJGQCIAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 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：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氯苄溴 在 palladium bromide 、 三(4-甲氧苯基)膦 、 sodium hexamethyldisilazane 、 silver benzoate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 为溶剂， 反应 17.33h， 生成 2-(2-chlorophenyl)pyrazolo[1,5-a]pyridine
  参考文献：
  名称：

  Synthesis of 2- and 2,3-Substituted Pyrazolo[1,5-a]pyridines: Scope and Mechanistic Considerations of a Domino Direct Alkynylation and Cyclization of N-Iminopyridinium Ylides Using Alkenyl Bromides, Alkenyl Iodides, and Alkynes

  摘要：

  Direct functionalization and tandem processes have both received considerable recent interest due to their cost and time efficiency. Herein we report the synthesis of difficult to obtain 2-substituted pyrazolo[1,5-a]pyridines through a tandem palladium-catalyzed/silver-mediated elimination/direct functionalization/cyclization reaction involving N-benzoyliminopyridinium ylides. As such, these biologically important molecules are prepared in an efficient, high-yielding manner, only requiring a two-step sequence from pyridine. Aryl-substituted alkenyl bromides and iodides are effective ylide coupling partners. Mechanistic studies led to the use of terminal alkynes, which extended the scope of the reaction to include alkyl substitution on the unsaturated reactive site. The optimization, scope, and mechanistic considerations of the process are discussed.

  DOI：

  10.1021/jo201303x

文献信息

• Synthesis of 2-Arylpyrazolo[1,5-a]pyridines by Suzuki–Miyaura Cross-Coupling Reaction
  作者：Shigeki Seto、Kentaro Umei、Yosuke Nishigaya、Megumi Kamiya、Yasushi Kohno

  DOI：10.1055/s-0034-1381025

  日期：——

  2-arylated pyrazolo[1,5-a]pyridine via pyrazolo[1,5-a]pyridine-2-yl triflate using the Suzuki–Miyaura­ ­­cross-coupling reaction is described. Fifteen 2-arylpyrazolo[1,5-a]pyridine derivatives were synthesized in 52–95% yields. Convenient access to a variety of 2-arylated pyrazolo[1,5-a]pyridine via pyrazolo[1,5-a]pyridine-2-yl triflate using the Suzuki–Miyaura­ ­­cross-coupling reaction is described. Fifteen

  摘要 方便地访问各种2-芳基化吡唑并[1,5-一个]吡啶吡唑并经由[1,5-一个]吡啶-2-基三氟甲磺酸酯使用被描述的Suzuki-Miyaura交叉偶联反应。合成了15种2-芳基吡唑并[1,5- a ]吡啶衍生物，产率为52-95％。 方便地访问各种2-芳基化吡唑并[1,5-一个]吡啶吡唑并经由[1,5-一个]吡啶-2-基三氟甲磺酸酯使用被描述的Suzuki-Miyaura交叉偶联反应。合成了15种2-芳基吡唑并[1,5- a ]吡啶衍生物，产率为52-95％。
• Synthesis of 2-Substituted Pyrazolo[1,5-<i>a</i>]pyridines through Cascade Direct Alkenylation/Cyclization Reactions
  作者：James J. Mousseau、Angélique Fortier、André B. Charette

  DOI：10.1021/ol902710f

  日期：2010.2.5

  from N-iminopyridinium ylides is described. These medicinally interesting compounds are formed through a cascade process involving a palladium-catalyzed direct alkenylation reaction followed by silver-mediated cyclization. The reaction can be performed with a wide range of electron-poor and electron-rich alkenyl iodides in good yields. This work represents perhaps the most direct route for the preparation

  描述了由N-亚氨基吡啶鎓的叶立德合成2-取代的吡唑并[1，5- a ]吡啶。这些医学上有趣的化合物是通过级联过程形成的，该过程涉及钯催化的直接烯基化反应，然后进行银介导的环化反应。该反应可与多种贫电子和富电子的烯基碘化物以高收率进行。这项工作可能代表了制备这些化合物的最直接途径。
• Synthesis of 2- and 2,3-Substituted Pyrazolo[1,5-<i>a</i>]pyridines: Scope and Mechanistic Considerations of a Domino Direct Alkynylation and Cyclization of <i>N</i>-Iminopyridinium Ylides Using Alkenyl Bromides, Alkenyl Iodides, and Alkynes
  作者：James J. Mousseau、James A. Bull、Carolyn L. Ladd、Angélique Fortier、Daniela Sustac Roman、André B. Charette

  DOI：10.1021/jo201303x

  日期：2011.10.21

  Direct functionalization and tandem processes have both received considerable recent interest due to their cost and time efficiency. Herein we report the synthesis of difficult to obtain 2-substituted pyrazolo[1,5-a]pyridines through a tandem palladium-catalyzed/silver-mediated elimination/direct functionalization/cyclization reaction involving N-benzoyliminopyridinium ylides. As such, these biologically important molecules are prepared in an efficient, high-yielding manner, only requiring a two-step sequence from pyridine. Aryl-substituted alkenyl bromides and iodides are effective ylide coupling partners. Mechanistic studies led to the use of terminal alkynes, which extended the scope of the reaction to include alkyl substitution on the unsaturated reactive site. The optimization, scope, and mechanistic considerations of the process are discussed.