9-(4-methylpyridin-2-yl)-3-nitro-9H-carbazole | 1570075-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-(4-methylpyridin-2-yl)-3-nitro-9H-carbazole
• CAS: 1570075-77-2
• 化学式: C₁₈H₁₃N₃O₂
• 分子量: 303.32
• InChiKey: VSEORWIZYDQIAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  60.96
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-溴-4-甲基吡啶 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium tert-butylate 、 copper diacetate 、 palladium diacetate 、 双(2-二苯基磷苯基)醚 、 对苯醌 作用下， 以 甲苯 、 叔丁醇 为溶剂， 反应 4.0h， 生成 9-(4-methylpyridin-2-yl)-3-nitro-9H-carbazole
  参考文献：
  名称：

  Palladium(II)-Catalyzed Direct Ortho Arylation of 4-Methyl-N-phenylpyridin-2-amines via C–H Activation/C–C Coupling and Synthetic Applications

  摘要：

  The direct ortho arylation of 4-methyl-N-phenylpyridin-2-amines via palladium(II)-catalyzed C-H activation is described. Treatment of 4-methyl-N-phenylpyridin-2-amine with potassium aryltrifluoroborate using 10 mol % of palladium(II) acetate as the catalyst, 2 equiv of copper(II) acetate as the oxidant, and 1 equiv of p-benzoquinone in tert-butyl alcohol gave ortho-arylated products in modest to excellent yields. This reaction shows good functional group compatibility. A series of H-1 NMR titration experiments and controlled experiments elucidating the reaction mechanism were carried out. The key intermediate, 4-methyl-N-phenylpyridin-2-amine palladacycle, was isolated and characterized by X-ray crystallography. The advanced transformations of ortho-phenylated 4-methyl-N-phenylpyridin-2-amine to N-(4-methylpyridin-2-yl)-9H-carbazole, biphenyl-2-amine, and 3-methyl-6-phenylpyrido[1,2-a]benzimidazole were successfully demonstrated as potential synthetic applications.

  DOI：

  10.1021/om401195w