3-bromo-5-(7-chloroquinolin-4-yl)isothiazole-4-carbonitrile | 1268248-02-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-bromo-5-(7-chloroquinolin-4-yl)isothiazole-4-carbonitrile
• CAS: 1268248-02-7
• 化学式: C₁₃H₅BrClN₃S
• 分子量: 350.626
• InChiKey: XIODRGXIZOXSTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.57
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  7-氯-4-碘喹啉 、 3-bromoisothiazole-4-carbonitrile 在 bis(triphenylphosphine)palladium(II) dichloride 、 silver fluoride 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以94%的产率得到3-bromo-5-(7-chloroquinolin-4-yl)isothiazole-4-carbonitrile
  参考文献：
  名称：

  Silver-Mediated Palladium-Catalyzed Direct C−H Arylation of 3-Bromoisothiazole-4-carbonitrile

  摘要：

  Silver(I) fluoride-mediated Pd-catalyzed C-H direct arylation/heteroarylation of 3-bromolsothiazole-4-carbonitrile (1a) gives twenty-four 5-aryl/heteroaryl-3-bromolsothiazole-4-carbonitriles. The reaction was partially optimized with respect to catalyst, ligand, and base. During this study 3,3'-dibromo-5,5'-blisothiazole-4,4'-dicarbonitrile (3a) was Isolated as a byproduct and subsequently prepared via the silver-mediated Pd-catalyzed oxidative dimerization of 3-bromolsothiazole-4-carbonitrile in 67% yield. The analogous phenylation and oxidative dimerization of 3-chloroisothiazole-4-carbonitrile (1b) gave 3-chloro-5-phenylIsothiazole-4-carbonitrile (4) and 3,3'-dichloro-5,5'-bilsothiazole-4,4'-dicarbonitrile (3b) In 96% and 69% yields, respectively.

  DOI：

  10.1021/ol200196m