4,N-Dimethyl-N-pyridin-2-yl-benzenesulfonamide | 65523-64-0

• 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: 4,N-Dimethyl-N-pyridin-2-yl-benzenesulfonamide
• 英文别名: N,4-dimethyl-N-pyridin-2-ylbenzenesulfonamide
• CAS: 65523-64-0
• 化学式: C₁₃H₁₄N₂O₂S
• 分子量: 262.332
• InChiKey: VHARWRWRNIPIDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-吡啶硼酸频那醇酯 、 N-甲基对甲苯磺酰胺 在 potassium phosphate 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 作用下， 以 乙腈 为溶剂， 以43%的产率得到4,N-Dimethyl-N-pyridin-2-yl-benzenesulfonamide
  参考文献：
  名称：

  Mechanistic Insight Enables Practical, Scalable, Room Temperature Chan–Lam N-Arylation of N-Aryl Sulfonamides

  摘要：

  Sulfonamides are profoundly important in pharmaceutical design. C-N cross-coupling of sulfonamides is an effective method for fragment coupling and structure-activity relationship (SAR) mining. However, cross-coupling of the important N-arylsulfonamide pharmacophore has been notably unsuccessful. Here, we present a solution to this problem via oxidative Cu catalysis (Chan-Lam cross-coupling). Mechanistic insight has allowed the discovery and refinement of an effective cationic Cu-catalyst to facilitate the practical and scalable Chan-Lam N-arylation of primary and secondary N-arylsulfonamides at room temperature. We also demonstrate utility in the large scale synthesis of a key intermediate to a clinical hepatitis C virus treatment.

  DOI：

  10.1021/acscatal.8b03238

文献信息

• Ruthenium-Catalyzed Remote C–H Sulfonylation of <i>N</i>-Aryl-2-aminopyridines with Aromatic Sulfonyl Chlorides
  作者：Balu Ramesh、Masilamani Jeganmohan

  DOI：10.1021/acs.orglett.7b03051

  日期：2017.11.3

  A ruthenium-catalyzed remote sulfonylation at the C5 position of the pyridine group of N-aryl-2-aminopyridines with aromatic sulfonyl chlorides is described. The mechanistic and deuterium labeling studies clearly reveal that the ruthenametallacycle is a key intermediate in the reaction, which forms via the C–H bond activation. The DFT calculation supports that the C5 position of the 2-aminopyridine

  描述了在N-芳基-2-氨基吡啶的吡啶基的吡啶基的C5位上用芳族磺酰氯进行钌催化的远程磺酰化。机理和氘标记研究清楚地表明，ruthenametallacycle是反应中的关键中间体，该反应是通过C–H键激活而形成的。DFT计算支持与金属杂环中间体中的其他碳相比，2-氨基吡啶基团的C5位置带有更多的负电荷（-0.304）。
• Mechanistic Insight Enables Practical, Scalable, Room Temperature Chan–Lam <i>N</i>-Arylation of <i>N</i>-Aryl Sulfonamides
  作者：Julien C. Vantourout、Ling Li、Enrique Bendito-Moll、Sonia Chabbra、Kenneth Arrington、Bela E. Bode、Albert Isidro-Llobet、John A. Kowalski、Mark G. Nilson、Katherine M. P. Wheelhouse、John L. Woodard、Shiping Xie、David C. Leitch、Allan J. B. Watson

  DOI：10.1021/acscatal.8b03238

  日期：2018.10.5

  Sulfonamides are profoundly important in pharmaceutical design. C-N cross-coupling of sulfonamides is an effective method for fragment coupling and structure-activity relationship (SAR) mining. However, cross-coupling of the important N-arylsulfonamide pharmacophore has been notably unsuccessful. Here, we present a solution to this problem via oxidative Cu catalysis (Chan-Lam cross-coupling). Mechanistic insight has allowed the discovery and refinement of an effective cationic Cu-catalyst to facilitate the practical and scalable Chan-Lam N-arylation of primary and secondary N-arylsulfonamides at room temperature. We also demonstrate utility in the large scale synthesis of a key intermediate to a clinical hepatitis C virus treatment.