N-(6-methylpyridin-3-yl)thiazol-2-amine | 1363337-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(6-methylpyridin-3-yl)thiazol-2-amine
• 英文别名: N-(6-methylpyridin-3-yl)-1,3-thiazol-2-amine
• CAS: 1363337-23-8
• 化学式: C₉H₉N₃S
• 分子量: 191.257
• InChiKey: VJENDCLOKWYOST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯噻唑 、 3-氨基-6-甲基吡啶 在 potassium tert-butylate 、 C₆₆H₉₂Cl₃N₃Pd 作用下， 以 正庚烷 为溶剂， 反应 4.0h， 以98%的产率得到N-(6-methylpyridin-3-yl)thiazol-2-amine
  参考文献：
  名称：

  Buchwald‐Hartwig Amination of Coordinating Heterocycles Enabled by Large‐but‐Flexible Pd‐BIAN‐NHC Catalysts**

  摘要：

  AbstractA new class of large‐but‐flexible Pd‐BIAN‐NHC catalysts (BIAN=acenaphthoimidazolylidene, NHC=N‐heterocyclic carbene) has been rationally designed to enable the challenging Buchwald‐Hartwig amination of coordinating heterocycles. This robust class of BIAN‐NHC catalysts permits cross‐coupling under practical aerobic conditions of a variety of heterocycles with aryl, alkyl, and heteroarylamines, including historically challenging oxazoles and thiazoles as well as electron‐deficient heterocycles containing multiple heteroatoms with BIAN‐INon (N,N′‐bis(2,6‐di(4‐heptyl)phenyl)‐7H‐acenaphtho[1,2‐d]imidazol‐8‐ylidene) as the most effective ligand. Studies on the ligand structure and electronic properties of the carbene center are reported. The study should facilitate the discovery of even more active catalyst systems based on the unique BIAN‐NHC scaffold.

  DOI：

  10.1002/chem.202103341

文献信息

• Palladium-Catalyzed N-Arylation of 2-Aminothiazoles
  作者：Meredeth A. McGowan、Jaclyn L. Henderson、Stephen L. Buchwald

  DOI：10.1021/ol300178j

  日期：2012.3.16

  A method for the Pd-catalyzed coupling of 2-aminothiazole derivatives with aryl bromides and triflates is described. Significantly, for this class of nucleophiles, the coupling exhibits a broad substrate scope and proceeds with a reasonable catalyst loading. Furthermore, an interesting effect of acetic acid as an additive is uncovered that facilitates catalyst activation.