3-(2-ethyl-4-methylthiazol-5-yl)-pyridine | 1109226-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2-ethyl-4-methylthiazol-5-yl)-pyridine
• 英文别名: 3-(2-ethyl-4-methylthiazol-5-yl)pyridine；2-Ethyl-4-methyl-5-pyridin-3-yl-1,3-thiazole
• CAS: 1109226-52-9
• 化学式: C₁₁H₁₂N₂S
• 分子量: 204.296
• InChiKey: MMOQWTFMOCKGPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴吡啶 、 2-乙基-4-甲基噻唑 在 PdCl(C₃H₅)(dppb) 、 potassium acetate 作用下， 以 戊醇 为溶剂， 反应 20.0h， 以70%的产率得到3-(2-ethyl-4-methylthiazol-5-yl)-pyridine
  参考文献：
  名称：

  Palladium-catalysed direct arylations of heteroaromatics using more eco-compatible solvents pentan-1-ol or 3-methylbutan-1-ol

  摘要：

  The palladium-catalysed direct coupling of aryl halides with heteroaromatics in greener solvents than DMF or DMAc, which are often employed for such couplings, would be a considerable advantage for both industrial application and sustainable development. We observed that a range of aryl bromides undergoe coupling via C-H bond activation/functionalisation reaction of thiazoles or imidazoles in moderate to good yields using pentan-1-ol or 3-methylbutan-1-ol as the solvents. Pentan-1-ol and 3-methylbutan-1-ol are less toxic than DMF or DMAc, moreover they are bioresources as they can be obtained by fermentation. Therefore, these reaction conditions are certainly more eco-compatible than those generally employed for such couplings. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.084

文献信息

• Palladium-catalyzed direct heteroarylation of chloropyridines and chloroquinolines
  作者：Fazia Derridj、Julien Roger、Florence Geneste、Safia Djebbar、Henri Doucet

  DOI：10.1016/j.jorganchem.2008.11.032

  日期：2009.2

  PdCl(dppb)(C3H5) as a catalyst, a range of heteroaryl derivatives undergoes coupling via C–H bond activation/functionalization reaction with chloropyridines or chloroquinolines in low to high yields. This air-stable catalyst can be used with a wide variety of substrates. The position of the chloro substituent on pyridines has a minor influence on the yields. On the other hand, the nature on the heteroaryl derivative

  芳基氯化物与杂芳烃的直接偶联将具有可持续发展的巨大优势，因为它们的成本更低，质量更轻，可用化合物的多样性更大，并且还因为仅形成了与副产物碱有关的HCl和减少制备这些化合物的步骤数。我们观察到通过使用PdCl（dppb）（C 3 H 5）作为催化剂，一系列杂芳基衍生物通过C–H键活化/官能化反应与氯吡啶或氯喹啉进行低至高收率的偶联。这种空气稳定的催化剂可与多种基材一起使用。吡啶上氯取代基的位置对收率影响很小。另一方面，杂芳基衍生物的性质具有很大的影响。使用苯并恶唑，噻吩或噻唑衍生物可获得最高的收率。氯吡啶与呋喃的偶联也得到了预期的产物，但是产率低至中等。