(4-Bromophenyl)-(2,6-difluoropyridin-3-yl)methanone | 1178521-37-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-Bromophenyl)-(2,6-difluoropyridin-3-yl)methanone
• CAS: 1178521-37-3
• 化学式: C₁₂H₆BrF₂NO
• 分子量: 298.087
• InChiKey: XACJRPZSPBUTPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-丙氨酸 、 (4-Bromophenyl)-(2,6-difluoropyridin-3-yl)methanone 在 一水合肼 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以55%的产率得到(2S)-2-[[3-(4-bromophenyl)-2H-pyrazolo[3,4-b]pyridin-6-yl]amino]propanoic acid
  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
• 作为产物：
  描述：

  2,6-二氟吡啶 、 4-溴-N-甲氧基-N-甲基苯胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以92%的产率得到(4-Bromophenyl)-(2,6-difluoropyridin-3-yl)methanone
  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

文献信息

• An efficient access to 3,6-disubstituted 1H-pyrazolo[3,4-b]pyridines via a one-pot double SNAr reaction and pyrazole formation
  作者：Yong-Li Zhong、Matthew G. Lindale、Nobuyoshi Yasuda

  DOI：10.1016/j.tetlet.2009.02.142

  日期：2009.5

  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.