2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine | 291743-95-8

• 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-(4-fluorophenyl)pyrazolo[1,5-a]pyridine
• CAS: 291743-95-8
• 化学式: C₁₃H₉FN₂
• 分子量: 212.226
• InChiKey: VQUNMLKSMQJXNQ-UHFFFAOYSA-N

物化性质

• 熔点：
  145-147 °C
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以85%的产率得到3-bromo-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine
  参考文献：
  名称：

  Au(i)-catalyzed and iodine-mediated cyclization of enynylpyrazoles to provide pyrazolo[1,5-a]pyridines

  摘要：

  吡唑并[1,5-a]吡啶和6-碘吡唑并[1,5-a]吡啶分别通过金催化、碘介导的烯丙基吡唑环化反应合成，收率良好至极佳。碘化加合物通过铃木-宫浦尔偶联反应进一步转化为6-芳基吡唑并[1,5-a]吡啶，通过乌尔曼缩合反应转化为6-氰基吡唑并[1,5-a]吡啶。其中一种环化加合物2-(4-氟苯基)吡唑并[1,5-a]吡啶通过两步反应转化为p38激酶抑制剂2-(4-氟苯基)-3-(4-吡啶基)吡唑并[1,5-a]吡啶。

  DOI：

  10.1039/c2ob25973g
• 作为产物：
  描述：

  N-iminopyridinium ylide 在 palladium bromide 、 三(4-甲氧苯基)膦 、 silver benzoate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 21.08h， 生成 2-(4-fluorophenyl)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

• Pyrazolo[1,5-a]pyridines as p38 Kinase Inhibitors
  作者：Kirk L. Stevens、David K. Jung、Michael J. Alberti、Jennifer G. Badiang、Gregory E. Peckham、Jim M. Veal、Mui Cheung、Philip A. Harris、Stanley D. Chamberlain、Michael R. Peel

  DOI：10.1021/ol0519745

  日期：2005.10.1

  [reaction: see text] A convergent synthesis of substituted pyrazolo[1,5-a]pyridines has been achieved either via a regioselective [3 + 2] cycloaddition of N-aminopyridines with alkynes or by thermal cyclization of disubstituted azirines. Subsequent palladium-catalyzed introduction of pyridines or de novo synthesis of pyrimidines affords inhibitors of p38 kinase.

  [反应：见正文]通过N-氨基吡啶与炔烃的区域选择性[3 + 2]环加成反应或双取代叠氮基的热环化，已实现了取代吡唑并[1,5-a]吡啶的收敛合成。随后钯催化的吡啶的引入或嘧啶的从头合成提供了p38激酶的抑制剂。
• Pyrazolopyridines
  申请人：SmithKline Beecham Corporation

  公开号：US06498166B1

  公开（公告）日：2002-12-24

  The invention provides the compounds of formula (I) wherein: R0 and R1 are independently selected from H, halogen, C1-6alkyl, C1-6alkoxy, or C1-6alkoxy substituted by one or more fluorine atoms; R2 is halogen, CN, CONR4R5, CO2H, CO2C1-6alkyl, or NHSO2R4; R3 is C1-6alkyl or NH2; and R4 and R5 are independently selected from H, C1-6alkyl, phenyl, phenyl substituted by one or more atoms or groups (selected from halogen, C1-6alkyl, C1-6alkoxy, or C1-6alkoxy substituted by one or more fluorine atoms), or together with the nitrogen atom to which they are attached form a saturated 4 to 8 membered ring; and pharmaceutically acceptable derivatives thereof. Compounds of formula (I) are potent and selective inhibitors of COX-2 and are of use in the treatment of the pain, fever, inflammation of a variety of conditions and diseases.

  该发明提供了以下式（I）的化合物：其中：R0和R1分别选择自H、卤素、C1-6烷基、C1-6烷氧基或由一个或多个氟原子取代的C1-6烷氧基；R2是卤素、CN、CONR4R5、CO2H、CO2C1-6烷基或NHSO2R4；R3是C1-6烷基或NH2；以及R4和R5分别选择自H、C1-6烷基、苯基、苯基取代一个或多个原子或基团（选择自卤素、C1-6烷基、C1-6烷氧基或由一个或多个氟原子取代的C1-6烷氧基），或与它们连接的氮原子一起形成饱和的4到8成员环；以及其药用可接受的衍生物。式（I）的化合物是强效和选择性的COX-2抑制剂，可用于治疗各种疾病和疾病的疼痛、发热、炎症。
• Fused pyrazole derivatives bieng protein kinase inhibitors
  申请人：——

  公开号：US20040053942A1

  公开（公告）日：2004-03-18

  Compounds of Formula (I): salts or solvates or physiologically functional derivatives thereof, wherein Z is CH or N, and R 1 , (R 2 , and R 4 are various substituent groups, are protein kinase inhibitors. 1

  式（I）化合物：其盐或溶剂合物或生理功能衍生物，其中Z为CH或N，R1，（R2和R4为各种取代基团，是蛋白激酶抑制剂。
• 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。
• Oxidative C–H/C–H Annulation of Imidazopyridines and Indazoles through Rhodium-Catalyzed Vinylene Transfer
  作者：Koushik Ghosh、Yuji Nishii、Masahiro Miura

  DOI：10.1021/acs.orglett.0c00975

  日期：2020.5.1

  Transition-metal-catalyzed C-H activation followed by oxidative annulation with alkynes has been an efficient synthetic tool for the assembly of various polyaromatic scaffolds. Despite the substantial progress in this field, it is still a significant challenge to achieve the synthesis of nonsubstituted vinylene-fused compounds. In this contribution, we report a Rh-catalyzed C-H/C-H vinylene cyclization adopting

  过渡金属催化的CH活化，然后与炔烃进行氧化环化反应，已成为组装各种聚芳烃支架的有效合成工具。尽管在该领域取得了很大进展，但是实现非取代的亚乙烯基稠合化合物的合成仍然是一个重大挑战。在这一贡献中，我们报告了采用碳酸亚乙烯酯作为“亚乙烯基转移”剂的Rh催化的CH / CH亚乙烯基环化反应。该协议实现了咪唑和吡唑融合的芳族化合物的直接环π延伸。