tert-butyl 4-[3-(4-bromophenyl)-2H-pyrazolo[3,4-b]pyridin-6-yl]piperazine-1-carboxylate | 1158955-36-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: tert-butyl 4-[3-(4-bromophenyl)-2H-pyrazolo[3,4-b]pyridin-6-yl]piperazine-1-carboxylate
• CAS: 1158955-36-2
• 化学式: C₂₁H₂₄BrN₅O₂
• 分子量: 458.358
• InChiKey: DNDFEQKARKBYEV-UHFFFAOYSA-N

物化性质

• 沸点：
  560.4±60.0 °C(predicted)
• 密度：
  1.47±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (4-Bromophenyl)-(2,6-difluoropyridin-3-yl)methanone 、 N-Boc-哌嗪 在 一水合肼 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以75%的产率得到tert-butyl 4-[3-(4-bromophenyl)-2H-pyrazolo[3,4-b]pyridin-6-yl]piperazine-1-carboxylate
  参考文献：
  名称：

  An efficient access to 3,6-disubstituted 1H-pyrazolo[3,4-b]pyridines via a one-pot double SNAr reaction and pyrazole formation

  摘要：

  A general and efficient synthetic method for the synthesis of biologically important series of 3,6-disubstituted-1H-pyrazolo[3,4-b]pyridines was discovered. 2,6-Difluoropyridine was deprotonated using 1.1 equiv of n-BuLi in THF at <-60 degrees C, followed by quenching with a variety of Weinreb amides to generate 2,6-Difluoro-3-ketopyridines in high yields. A mild tandem reaction sequence of selective nucleophilic Substitution of the 6-fluoride with a variety of nucleophiles, followed by hydrazine substitution of the 2-fluoride and pyrazole formation in a one-pot fashion afforded a series of 3,6-disubstituted-1H-pyrazolo[3,4-b]pyridines in moderate to good yields. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.142