3-(5-bromopyrimidin-2-yloxy)benzoic acid methyl ester | 1147704-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(5-bromopyrimidin-2-yloxy)benzoic acid methyl ester
• 英文别名: 3-(5-Bromo-pyrimidin-2-yloxy)-benzoic Acid Methyl Ester；methyl 3-(5-bromopyrimidin-2-yl)oxybenzoate
• CAS: 1147704-08-2
• 化学式: C₁₂H₉BrN₂O₃
• 分子量: 309.119
• InChiKey: GUMDGFYFYBUNLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  61.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(5-bromo-pyrimidin-2-yloxy)-3H-[1,2,3]triazolo[4,5-b]pyridine 、 3-甲氧基羰基苯硼酸 在 四(三苯基膦)钯 、 氧气 、 caesium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 10.0h， 以33%的产率得到3-(5-bromopyrimidin-2-yloxy)benzoic acid methyl ester
  参考文献：
  名称：

  芳基硼酸氧化吡啶并三唑-1-酰氧基嘧啶的钯催化杂芳基醚

  摘要：

  在含有0.6-1.0％H 2 O的DME中，在Cs 2 CO 3存在下，含吡啶三唑-1-基氧基（O Pt）作为脲或酰胺官能团的嘧啶与芳基硼酸的氧化钯催化交叉偶联。描述了制备杂芳基醚的方法。在3-（5-溴-嘧啶-2-基氧基）-3 H- [1,2,3]三唑并[4,5- b ]吡啶1的情况下，溴取代可作为进一步处理的手段，例如作为Suzuki偶联剂，用于连接各种芳基。

  DOI：

  10.1021/ol900592b

文献信息

• Heteroaryl Ethers by Oxidative Palladium Catalysis of Pyridotriazol-1-yloxy Pyrimidines with Arylboronic Acids
  作者：Sujata Bardhan、Sumrit Wacharasindhu、Zhao-Kui Wan、Tarek S. Mansour

  DOI：10.1021/ol900592b

  日期：2009.6.18

  The oxidative palladium-catalyzed cross-coupling of pyrimidines containing pyridotriazol-1-yloxy (OPt) as either a urea or an amide functional group with arylboronic acids in the presence of Cs2CO3 in DME containing 0.6−1.0% H2O is described for the preparation of heteroaryl ethers. The bromo substitution in the case of 3-(5-bromo-pyrimidin-2-yloxy)-3H-[1,2,3]triazolo[4,5-b]pyridine 1 could serve as

  在含有0.6-1.0％H 2 O的DME中，在Cs 2 CO 3存在下，含吡啶三唑-1-基氧基（O Pt）作为脲或酰胺官能团的嘧啶与芳基硼酸的氧化钯催化交叉偶联。描述了制备杂芳基醚的方法。在3-（5-溴-嘧啶-2-基氧基）-3 H- [1,2,3]三唑并[4,5- b ]吡啶1的情况下，溴取代可作为进一步处理的手段，例如作为Suzuki偶联剂，用于连接各种芳基。
• HETEROARYL ETHERS AND PROCESSES FOR THEIR PREPARATION
  申请人：Mansour Tarek Suhayl

  公开号：US20090291971A1

  公开（公告）日：2009-11-26

  The present invention relates to processes for the preparation of heteroaryl ethers. In some embodiments, the processes relate to cross coupling reactions between triazol-1-yloxy and triazol-1-yl heterocycles with aryl boronic acids. In a further aspect, this invention also relates to compounds that are useful for the treatment of oncological diseases or disorders, and for the treatment of inflammation.

  本发明涉及制备杂环基醚的过程。在某些实施例中，该过程涉及三唑-1-氧基和三唑-1-基杂环与芳基硼酸之间的交叉偶联反应。在进一步的方面，本发明还涉及用于治疗肿瘤疾病或障碍以及治疗炎症的化合物。
• [EN] HETEROARYL ETHERS AND PROCESSES FOR THEIR PREPARATION<br/>[FR] HÉTÉROARYL ÉTHERS ET LEURS PROCÉDÉS DE PRÉPARATION
  申请人：WYETH CORP

  公开号：WO2009058937A2

  公开（公告）日：2009-05-07

  The present invention relates to processes for the preparation of of heteroaryl ethers. In some embodiments, the processes relate to cross coupling reactions between triazol-1-yloxy and triazol-1-yl heterocycles with aryl boronic acids. In a further aspect, this invention also relates to compounds that are useful for the treatment of oncological diseases or disorders, and for the treatment of inflammation.
• Hydrogen peroxide mediated formation of heteroaryl ethers from pyridotriazol-1-yloxy heterocycles and arylboronic acids
  作者：Sujata Bardhan、Keiko Tabei、Zhao-Kui Wan、Tarek S. Mansour

  DOI：10.1016/j.tetlet.2009.07.135

  日期：2009.10

  Pyridotriazol-1-yloxypyrimidine 3 reacts with arylboronic acids under palladium-free, Cs2CO3, (0.8%) H2O2, and DME conditions to produce heteroaryl ethers 4-16 in good yields comparable to the oxidative palladium-catalyzed reaction. The yields of aryl ethers 17-19 from quinazoline 2 with (0.8%) H2O2 were modest. Hydrogen peroxide is Superior to dioxygen as an oxidant in these reactions. (C) 2009 Elsevier Ltd. All rights reserved.