(6-Bromopyridin-3-yl)-piperazin-1-ylmethanone;2,2,2-trifluoroacetic acid | 1398603-39-8

• 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: (6-Bromopyridin-3-yl)-piperazin-1-ylmethanone;2,2,2-trifluoroacetic acid
• 英文别名: (6-bromopyridin-3-yl)-piperazin-1-ylmethanone;2,2,2-trifluoroacetic acid
• CAS: 1398603-39-8
• 化学式: C₂HF₃O₂*C₁₀H₁₂BrN₃O
• 分子量: 384.153
• InChiKey: GVSRIIOWAZASJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (6-Bromopyridin-3-yl)-piperazin-1-ylmethanone;2,2,2-trifluoroacetic acid 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 0.29h， 生成
  参考文献：
  名称：

  Rapid Access to Compound Libraries through Flow Technology: Fully Automated Synthesis of a 3-Aminoindolizine Library via Orthogonal Diversification

  摘要：

  A novel methodology for the synthesis of druglike heterocycle libraries has been developed through the use of flow reactor technology. The strategy employs orthogonal modification of a heterocyclic core, which is generated in situ, and was used to construct both a 25-membered library of druglike 3-aminoindolizines, and selected examples of a 100-member virtual library. This general protocol allows a broad range of acylation, alkylation and sulfonamidation reactions to be performed in conjunction with a tandem Sonogashira coupling/cycloisomerization sequence. All three synthetic steps were conducted under full automation in the flow reactor, with no handling or isolation of intermediates, to afford the desired products in good yields. This fully automated, multistep flow approach opens the way to highly efficient generation of druglike heterocyclic systems as part of a lead discovery strategy or within a lead optimization program.

  DOI：

  10.1021/co300094n

文献信息

• Rapid Access to Compound Libraries through Flow Technology: Fully Automated Synthesis of a 3-Aminoindolizine Library via Orthogonal Diversification
  作者：Paul P. Lange、Keith James

  DOI：10.1021/co300094n

  日期：2012.10.8

  A novel methodology for the synthesis of druglike heterocycle libraries has been developed through the use of flow reactor technology. The strategy employs orthogonal modification of a heterocyclic core, which is generated in situ, and was used to construct both a 25-membered library of druglike 3-aminoindolizines, and selected examples of a 100-member virtual library. This general protocol allows a broad range of acylation, alkylation and sulfonamidation reactions to be performed in conjunction with a tandem Sonogashira coupling/cycloisomerization sequence. All three synthetic steps were conducted under full automation in the flow reactor, with no handling or isolation of intermediates, to afford the desired products in good yields. This fully automated, multistep flow approach opens the way to highly efficient generation of druglike heterocyclic systems as part of a lead discovery strategy or within a lead optimization program.