(2-对甲苯-咪唑并[1,2-a]吡啶-3-基)-乙腈 | 885272-74-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (2-对甲苯-咪唑并[1,2-a]吡啶-3-基)-乙腈
• 英文名称: 2-(2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)acetonitrile
• 英文别名: 2-[2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetonitrile
• CAS: 885272-74-2
• 化学式: C₁₆H₁₃N₃
• 分子量: 247.299
• InChiKey: KFXYMUPAEISGJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4-甲基苯基)咪唑并[1,2-a]吡啶 在 溶剂黄146 、 碘甲烷 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 32.0h， 生成 (2-对甲苯-咪唑并[1,2-a]吡啶-3-基)-乙腈
  参考文献：
  名称：

  Lange; Karolak-Wojciechowska; Wejroch, Acta poloniae pharmaceutica, 2001, vol. 58, # 1, p. 43 - 52

  摘要：

  DOI：

文献信息

• One‐Pot Synthesis of C3‐Alkylated Imidazopyridines from α‐Bromocarbonyls under Photoredox Conditions
  作者：Jinwen Tong、Yanling Zhan、Jingyu Li、Ping Liu、Peipei Sun

  DOI：10.1002/ejoc.202100922

  日期：2021.8.26

  One pot condensation and alkylation of α-bromocarbonyl compounds with 2-aminopyridines to access C3-alkylated imidazopyridines were achieved through photoredox catalysis. Comparing with the traditional route, this protocol provided an efficient and green synthesis of zolpidem in a short synthesis.

  通过光氧化还原催化，α-溴羰基化合物与 2-氨基吡啶的一锅缩合和烷基化得到C3-烷基化的咪唑并吡啶。与传统路线相比，该方案在短合成中提供了唑吡坦的高效绿色合成。
• Iron-Catalyzed Dehydrogenative sp³–sp² Coupling via Direct Oxidative C–H Activation of Acetonitrile
  作者：Huimin Su、Luyao Wang、Honghua Rao、Hao Xu

  DOI：10.1021/acs.orglett.7b00678

  日期：2017.5.5

  An iron-catalyzed dehydrogenative sp3–sp2 coupling of acetonitrile and 2-arylimidazo[1,2-a]pyridine has been realized, which can serve as a novel approach toward heteroarylacetonitriles. The merit of this strategy is illustrated by the breadth of functional groups tolerated in the transformation and the fast access to pharmaceuticals (such as zolpidem) directly from the heteroarylacetonitriles.

  乙腈与2-芳基咪唑[1,2- a ]吡啶的铁催化的sp 3 –sp 2脱氢偶联反应已经实现，可以作为杂芳基乙腈的一种新方法。该策略的优点通过转化中可耐受的官能团的广度以及直接从杂芳基乙腈快速获得药品（如唑吡坦）来说明。
• Visible-Light-Induced Regioselective Cyanomethylation of Imidazopyridines and Its Application in Drug Synthesis
  作者：Qing Chang、Zhengyi Liu、Ping Liu、Lu Yu、Peipei Sun

  DOI：10.1021/acs.joc.7b00750

  日期：2017.5.19

  3-Cyanomethylated imidazopyridines were synthesized via a visible light-promoted reaction of imidazopyridines with bromoacetonitrile or iodoacetonitrile catalyzed by fac-Ir(ppy)3 under mild conditions. For the substrates with various substituents on benzene or pyridine ring, the reaction proceeded smoothly to give the corresponding products in moderate to good yields. The synthetic utility of this

  通过fac -Ir（ppy）3在温和条件下催化的咪唑并吡啶与溴乙腈或碘乙腈的可见光促进反应合成了3-氰基甲基化的咪唑并吡啶。对于在苯或吡啶环上具有各种取代基的底物，反应平稳进行，以中等至良好的产率得到相应的产物。这种可见光诱导的反应的合成效用已经在唑吡坦和阿吡坦的有效合成中得到了说明。
• Synthesis of C3-Cyanomethylated Imidazo[1,2-a]pyridines via Ultrasound-Promoted Three-Component Reaction under Catalyst- and Oxidant-Free Conditions
  作者：Jie Zhang、Haifeng Yang、Yufeng Zhang、Jian Zhang、Qingguo Wu

  DOI：10.1055/a-1704-4822

  日期：2022.2

  An efficient synthesis of C3-cyanomethylated imidazo[1,2-a]pyridines via ultrasound-promoted three-component reaction under catalyst-free, oxidant-free, and mild conditions has been developed. A series of C3-cyanomethylated imidazo[1,2-a]pyridines were rapidly prepared with satisfactory yields and good functional group compatibility. This strategy cloud also be applied to the synthesis of zolpidem and

  开发了一种在无催化剂、无氧化剂和温和条件下通过超声促进的三组分反应高效合成 C3-氰基甲基化咪唑并[1,2-a]吡啶的方法。以令人满意的收率和良好的官能团相容性快速制备了一系列C3-氰甲基化咪唑并[1,2-a]吡啶。该策略云也适用于短步骤合成唑吡坦和阿匹坦。
• [EN] PROCESS FOR PREPARING ZOLPIDEM AND ITS INTERMEDIATE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE ZOLPIDÉM ET DE SON INTERMÉDIAIRE
  申请人：SUVEN LIFE SCIENCES LTD

  公开号：WO2009007995A1

  公开（公告）日：2009-01-15

  The present invention relates to an improved process for the preparation of 6- methyl-2-[4-methylphenyl]imidazo[l,2-a]pyridine-3-N,N-dimethyl acetamide having formula (1). The compound of formula (1) has adopted name 'Zolpidem'. The present invention also relates to novel intermediate of the formula (2) and a process for its preparation.Wherein R represents methyl, ethyl, propyl, butyl, isopropyl, isobutyl or tertiary butyl group. The novel intermediate of formula (2) is used in preparation of Zolpidem having formula (1). Zolpidem is useful in the treatment of anxiety, sleep disorders and convulsion.

  本发明涉及一种改进的制备6-甲基-2-[4-甲基苯基]咪唑[1,2-a]吡啶-3-N,N-二甲基乙酰胺（化学式（1））的方法。化合物化学式（1）的通用名称为“唑吡坦”。本发明还涉及化学式（2）的新型中间体及其制备方法。其中R代表甲基、乙基、丙基、丁基、异丙基、异丁基或叔丁基基团。化学式（2）的新型中间体用于制备化合物化学式（1）的唑吡坦。唑吡坦在治疗焦虑、睡眠障碍和惊厥方面具有用途。