3-<1-(4-Bromo-2-oxo-1,2-dihydro-3-pyridyl)ethyl>indol | 137719-07-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-<1-(4-Bromo-2-oxo-1,2-dihydro-3-pyridyl)ethyl>indol
• 英文别名: 4-bromo-3-[1-(1H-indol-3-yl)ethyl]-1H-pyridin-2-one
• CAS: 137719-07-4
• 化学式: C₁₅H₁₃BrN₂O
• 分子量: 317.185
• InChiKey: ZPRGMSVSBIZDBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  48.65
• 氢给体数：
  2.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-氟吡啶 在 对甲苯磺酸 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 3-<1-(4-Bromo-2-oxo-1,2-dihydro-3-pyridyl)ethyl>indol
  参考文献：
  名称：

  A new convergent route to 1-substituted ellipticines

  摘要：

  1-(2-Fluoro-4-pyridyl)ethanone was synthesized from 2-fluoropyridine and was ortho-lithiated after activation as the propylene glycol ketal. The resulting 3-lithio derivative was trapped by various electrophiles but reacted in low yield with N-protected 3-indolecarbaldehyde. Model compounds 1-[[[2-(diethylamino)ethyl]amino]-3-pyridyl]ethanol and -ethanone were prepared and selectively condensed with indole. 1-[[[2-(Diethylamino)-ethyl]amino]-3-pyridyl]ethanol and -ethanone bearing a ketal-protected acetyl moiety at the C-4 position have been obtained in high yields starting from the propylene glycol ketal of 1-(2-fluoro-4-pyridyl)ethanone. These reagents could not be condensed with indole either due to side reactions between the C-3 and C-4 functions or to steric hindrance. 1-(2-Substituted-4-bromo-3-pyridyl)ethanols were synthesized via a metalation/halogen-dance strategy starting from 2-fluoropyridine. 1-(2,4-Dihalo-3-pyridyl)-1-chloroethane could be prepared and condensed with 1-indolylmagnesium iodide, which allowed the construction of the expected 3-[1-(3-pyridyl)ethyl]indole skeleton. Functionalization of the pyridine C-4 bromo position was achieved by a vinylstannane cross-coupling reaction using a palladium(0) catalyst. Acidic treatment of the resulting 4-(1-ethoxyethenyl)pyridine led to 1-fluoroellipticine. The whole sequence requires six steps from indole and 2-fluoropyridine and allows an attractive overall yield.

  DOI：

  10.1021/jo00028a032