3-bromo-6-(pyridin-3-yloxy)pyridine | 900493-23-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-bromo-6-(pyridin-3-yloxy)pyridine
• 英文别名: 5-Bromo-2-(pyridin-3-yloxy)pyridine；5-bromo-2-pyridin-3-yloxypyridine
• CAS: 900493-23-4
• 化学式: C₁₀H₇BrN₂O
• 分子量: 251.082
• InChiKey: JBEQHXPNQXLTEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 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：
  35
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

SDS

5-BROMO-2-(PYRIDIN-3-YLOXY)PYRIDINEMSDS英文版

反应信息

• 作为反应物：
  描述：

  3-bromo-6-(pyridin-3-yloxy)pyridine 在 正丁基锂 、 硼酸三异丙酯 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以8%的产率得到B-[6-(3-吡啶氧基)-3-吡啶]-硼酸
  参考文献：
  名称：

  Novel oxybispyridylboronic acids: synthesis and study of their reactivity in Suzuki-type cross-coupling reactions

  摘要：

  This paper sets forth the synthesis of novel oxybispyridylboronic acids, which are prepared from the corresponding halo-oxybispyridines via halogen-metal exchange using n-butyllithium and treatment with triisopropylborate. A range of efficient cross-coupling reactions of these novel boronic acids with selected aryl halides is described. This strategy produces novel pyridylethers of interest in cholinergic medicinal chemistry. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.036
• 作为产物：
  描述：

  3-羟基吡啶 、 2,5-二溴吡啶 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 以66%的产率得到3-bromo-6-(pyridin-3-yloxy)pyridine
  参考文献：
  名称：

  Synthesis of novel halo-oxybispyridines, new building blocks in cholinergic medicinal chemistry

  摘要：

  This paper describes a method for the preparation of oxybispyridines bearing several halogens, which could be further transformed into other functional groups thus giving access to libraries with the bis-pyridyl ether moiety as the common structural feature of interest in cholinergic medicinal chemistry. Scope and limitation of the method are outlined. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.002

文献信息

• Radical and ionic <i>meta</i> -C–H functionalization of pyridines, quinolines, and isoquinolines
  作者：Hui Cao、Qiang Cheng、Armido Studer

  DOI：10.1126/science.ade6029

  日期：2022.11.18

  Carbon-hydrogen (C−H) functionalization of pyridines is a powerful tool for the rapid construction and derivatization of many agrochemicals, pharmaceuticals, and materials. Because of the inherent electronic properties of pyridines, selective meta -C−H functionalization is challenging. Here, we present a protocol for highly regioselective meta -C−H trifluoromethylation, perfluoroalkylation, chlorination

  吡啶的碳氢 (C−H) 功能化是快速构建和衍生许多农用化学品、药物和材料的有力工具。由于吡啶固有的电子特性，选择性元-C−H 功能化具有挑战性。在这里，我们提出了一个高度区域选择性的协议元-C−H 三氟甲基化、全氟烷基化、氯化、溴化、碘化、硝化、硫烷基化和吡啶硒基化通过氧化还原-中性脱芳构化-重芳构化过程。引入的脱芳烃活化模式为通过自由基和离子途径对吡啶和其他氮杂芳烃进行间位选择性反应提供了多样化平台。这些无催化剂反应的广泛范围和高选择性使这些过程适用于药物的后期功能化。
• C–H Functionalization of Pyridines via Oxazino Pyridine Intermediates: Switching to <i>para</i>-Selectivity under Acidic Conditions
  作者：Hui Cao、Debkanta Bhattacharya、Qiang Cheng、Armido Studer

  DOI：10.1021/jacs.3c05242

  日期：2023.7.19

  para-Selective C–H functionalization of pyridines holds a significant value but remains underdeveloped. Site-switchable C–H functionalization of pyridines under easily tunable conditions expedites drug development. We recently reported a redox-neutral dearomatization–rearomatization strategy for meta-C–H functionalization of pyridines via oxazino pyridine intermediates. Here, we demonstrate that these

  吡啶的对位选择性 C-H 官能化具有重要价值，但仍不成熟。在易于调节的条件下对吡啶进行位点可切换的 C-H 官能化可加快药物开发。我们最近报道了一种通过恶嗪吡啶中间体对吡啶进行间-C-H功能化的氧化还原中性脱芳构化-重芳构化策略。在这里，我们证明这些恶嗪吡啶中间体只需切换到酸性条件即可进行高度对位选择性官能化。多种对烷基化和芳基化吡啶是通过自由基和离子途径制备的。这些温和且无催化剂的方法适用于使用吡啶作为限制试剂的药物的后期对位官能化。吡啶的连续间位、对位双官能化也可以通过依赖于恶嗪吡啶的 pH 依赖性反应性的完全区域控制来实现。
• Structure-Guided Elaboration of a Fragment-Like Hit into an Orally Efficacious Leukotriene A4 Hydrolase Inhibitor
  作者：Gebhard Thoma、Wolfgang Miltz、Honnappa Srinivas、Carlos A. Penno、Michael Kiffe、Monika Gajewska、Kai Klein、Amanda Evans、Christian Beerli、Till A. Röhn

  DOI：10.1021/acs.jmedchem.4c00290

  日期：2024.3.28

  Leukotriene A4 hydrolase (LTA4H) is the final and rate-limiting enzyme in the biosynthesis of pro-inflammatory leukotriene B4 (LTB4). Preclinical studies have provided strong evidence that LTA4H is an attractive drug target for the treatment of chronic inflammatory diseases. Here, we describe the transformation of compound 2, a fragment-like hit, into the potent inhibitor of LTA4H 3. Our strategy involved

  白三烯 A4 水解酶 (LTA4H) 是促炎白三烯 B4 (LTB 4 ) 生物合成中的最终限速酶。临床前研究提供了强有力的证据，表明LTA4H是治疗慢性炎症性疾病的一个有吸引力的药物靶点。在这里，我们描述了化合物2 （一种类似片段的命中）转化为 LTA4H 3的有效抑制剂。我们的策略涉及两个关键步骤。首先，我们的目标是增加片段2的极性，以改善其药物相似性，特别是其溶解度，同时保留其有希望的效力和低分子量。其次，我们利用结构信息并整合了基本氨基功能，从而可以与 LTA4H 的 Q136 形成必要的氢键，从而增强了效力。化合物3表现出卓越的选择性，并在 KRN 被动血清诱导的小鼠关节炎模型中显示出口服功效。在谷浓度下达到 90% 目标参与度的预期人体剂量确定为每日一次 40 mg。
• Synthesis of novel halo-oxybispyridines, new building blocks in cholinergic medicinal chemistry
  作者：Anne Sophie Voisin、Alexandre Bouillon、Jean-Charles Lancelot、Aurélien Lesnard、Sylvain Rault

  DOI：10.1016/j.tet.2006.04.002

  日期：2006.6

  This paper describes a method for the preparation of oxybispyridines bearing several halogens, which could be further transformed into other functional groups thus giving access to libraries with the bis-pyridyl ether moiety as the common structural feature of interest in cholinergic medicinal chemistry. Scope and limitation of the method are outlined. (c) 2006 Elsevier Ltd. All rights reserved.
• Novel oxybispyridylboronic acids: synthesis and study of their reactivity in Suzuki-type cross-coupling reactions
  作者：Anne Sophie Voisin、Alexandre Bouillon、Inmaculada Berenguer、Jean-Charles Lancelot、Aurélien Lesnard、Sylvain Rault

  DOI：10.1016/j.tet.2006.09.036

  日期：2006.12

  This paper sets forth the synthesis of novel oxybispyridylboronic acids, which are prepared from the corresponding halo-oxybispyridines via halogen-metal exchange using n-butyllithium and treatment with triisopropylborate. A range of efficient cross-coupling reactions of these novel boronic acids with selected aryl halides is described. This strategy produces novel pyridylethers of interest in cholinergic medicinal chemistry. (c) 2006 Elsevier Ltd. All rights reserved.