8-Methoxy-3-methyl-5-(3-methylphenyl)imidazo[1,5-a]pyrazine | 1040751-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并[1,5-a]吡嗪
• 英文名称: 8-Methoxy-3-methyl-5-(3-methylphenyl)imidazo[1,5-a]pyrazine
• CAS: 1040751-66-3
• 化学式: C₁₅H₁₅N₃O
• 分子量: 253.304
• InChiKey: IGUINUCEJHCARP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  8-methoxy-3-methylimidazo[1,5-a]pyrazine 、 3-溴甲基苯 在 di-tert-butyl(methyl)phosphonium tetrafluoroborate salt 、 palladium diacetate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以92%的产率得到8-Methoxy-3-methyl-5-(3-methylphenyl)imidazo[1,5-a]pyrazine
  参考文献：
  名称：

  Palladium-Catalyzed Direct Heck Arylation of Dual π-Deficient/π-Excessive Heteroaromatics. Synthesis of C-5 Arylated Imidazo[1,5-a]pyrazines

  摘要：

  A general and efficient synthesis of 5-aryl imidazo[1,5-a]pyrazines by palladium-catalyzed coupling of the corresponding 8-substituted derivatives with aryl halides is described. The scope of this new reaction for the imidazo[1,5-a]pyrazine ring system was explored using three readily available 8-substituted precursors, X = NH2, NMe2, and OMe, as well as 8-aryl derivatives, X = Ar'. On the basis of these results as well as studies using a deuterated derivative, a Heck-like mechanism is proposed for this transformation.

  DOI：

  10.1021/ol800761r