2-bromo-4-(4-methanesulfonylpiperazin-1-ylmethyl)aniline | 850171-04-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-4-(4-methanesulfonylpiperazin-1-ylmethyl)aniline
• 英文别名: 2-Bromo-4-[(4-methylsulfonylpiperazin-1-yl)methyl]aniline
• CAS: 850171-04-9
• 化学式: C₁₂H₁₈BrN₃O₂S
• 分子量: 348.264
• InChiKey: PKSBFHOXFSNDAS-UHFFFAOYSA-N

物化性质

• 熔点：
  117-118 °C
• 沸点：
  468.8±55.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-bromo-4-(4-methanesulfonylpiperazin-1-ylmethyl)aniline 在 palladium diacetate 磷酸 、 三乙胺 、 三(邻甲基苯基)磷 、 亚磷酸三乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-methoxy-3-(5-{[4-(methylsulfonyl)-1-piperazinyl]-methyl}-1H-indol-2-yl)-quinoline
  参考文献：
  名称：

  Synthesis of 5-Substituted-1H-indol-2-yl-1H-quinolin-2-ones:  A Novel Class of KDR Kinase Inhibitors

  摘要：

  A number of approaches for the synthesis of the 1H-indol-2-yl-1H-quinolin-2-one ring system found in the potent and selective KDR kinase inhibitor 1 are described. The preparation and reaction of trimethylsilylnitrobenzene 26 with 2-methoxy-3-quinolinecarboxaldehyde 28 afforded alcohol 30, which was the key intermediate for the preparation of the target compounds. Conversion of alcohol 30 to either nitroketone 36 or nitrostyrene 45 set the stage for reductive cyclization and the formation of indole 25. The quinolin-2-one functionality was unmasked in the last step to provide compound 1 in 56-60% overall yield from readily available starting materials.

  DOI：

  10.1021/jo0480545
• 作为产物：
  描述：

  1-[(4-硝基苯基)甲基]哌嗪 在 ammonium heptamolybdate 、 palladium on activated charcoal sodium perborate 、 氢气 、 溶剂黄146 、 三乙胺 、 potassium bromide 作用下， 以 醋酸异丙酯 、 乙酸乙酯 为溶剂， 20.0 ℃ 、103.42 kPa 条件下， 反应 12.5h， 生成 2-bromo-4-(4-methanesulfonylpiperazin-1-ylmethyl)aniline
  参考文献：
  名称：

  Synthesis of 5-Substituted-1H-indol-2-yl-1H-quinolin-2-ones:  A Novel Class of KDR Kinase Inhibitors

  摘要：

  A number of approaches for the synthesis of the 1H-indol-2-yl-1H-quinolin-2-one ring system found in the potent and selective KDR kinase inhibitor 1 are described. The preparation and reaction of trimethylsilylnitrobenzene 26 with 2-methoxy-3-quinolinecarboxaldehyde 28 afforded alcohol 30, which was the key intermediate for the preparation of the target compounds. Conversion of alcohol 30 to either nitroketone 36 or nitrostyrene 45 set the stage for reductive cyclization and the formation of indole 25. The quinolin-2-one functionality was unmasked in the last step to provide compound 1 in 56-60% overall yield from readily available starting materials.

  DOI：

  10.1021/jo0480545

文献信息

• Synthesis of 5-Substituted-1<i>H</i>-indol-2-yl-1<i>H</i>-quinolin-2-ones:  A Novel Class of KDR Kinase Inhibitors
  作者：Jeffrey T. Kuethe、Audrey Wong、Chuanxing Qu、Jacqueline Smitrovich、Ian W. Davies、David L. Hughes

  DOI：10.1021/jo0480545

  日期：2005.4.1

  A number of approaches for the synthesis of the 1H-indol-2-yl-1H-quinolin-2-one ring system found in the potent and selective KDR kinase inhibitor 1 are described. The preparation and reaction of trimethylsilylnitrobenzene 26 with 2-methoxy-3-quinolinecarboxaldehyde 28 afforded alcohol 30, which was the key intermediate for the preparation of the target compounds. Conversion of alcohol 30 to either nitroketone 36 or nitrostyrene 45 set the stage for reductive cyclization and the formation of indole 25. The quinolin-2-one functionality was unmasked in the last step to provide compound 1 in 56-60% overall yield from readily available starting materials.