2,6-二溴-3-甲氧基吡啶 | 79491-45-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 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
• 中文名称: 2,6-二溴-3-甲氧基吡啶
• 英文名称: 2,6-dibromo-3-methoxypyridine
• CAS: 79491-45-5
• 化学式: C₆H₅Br₂NO
• 分子量: 266.92
• InChiKey: JFWDQTIVECPBDE-UHFFFAOYSA-N

物化性质

• 熔点：
  99-100 °C(Solv: hexane (110-54-3))
• 沸点：
  294.5±35.0 °C(Predicted)
• 密度：
  1.919±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储条件为2-8°C，并需保存在惰性气体中。

反应信息

• 作为反应物：
  描述：

  2,6-二溴-3-甲氧基吡啶 在 硫酸 、 硝酸 、 potassium nitrate 作用下， 以31%的产率得到2,6-二溴-3-甲氧基-5-硝基吡啶
  参考文献：
  名称：

  [EN] COMPOUNDS FOR THE TREATMENT OF KINASE-DEPENDENT DISORDERS
  [FR] COMPOSÉS DESTINÉS AU TRAITEMENT DE TROUBLES DÉPENDANT DE LA KINASE

  摘要：

  本文披露了公式I'的化合物。公式I'的化合物抑制、调节和/或调控激酶受体，尤其是与细胞活动变化相关的Axl和Mer信号传导途径，包含这些化合物的组合物，并使用它们治疗激酶依赖性疾病和病况的方法。本发明还提供了制备上述化合物的方法和包含这些化合物的组合物。

  公开号：

  WO2019148043A1
• 作为产物：
  描述：

  3-羟基吡啶 在 溴 、 potassium carbonate 、 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 28.0h， 生成 2,6-二溴-3-甲氧基吡啶
  参考文献：
  名称：

  Phosphoinositide-3-kinase inhibitors: Evaluation of substituted alcohols as replacements for the piperazine sulfonamide portion of AMG 511

  摘要：

  Replacement of the piperazine sulfonamide portion of the PI3K alpha inhibitor AMG 511 (1) with a range of aliphatic alcohols led to the identification of a truncated gem-dimethylbenzylic alcohol analog, 2-(5-(4-amino- 6-methyl-1,3,5-triazin-2-yl)-6-((5-fluoro-6-methoxypyridin-3-yl) amino) pyridin-3-yl) propan-2-ol (7). This compound possessed good in vitro efficacy and pharmacokinetic parameters and demonstrated an EC50 of 239 ng/mL in a mouse liver pharmacodynamic model measuring the inhibition of hepatocyte growth factor (HGF)-induced Akt Ser473 phosphorylation in CD1 nude mice 6 h post-oral dosing. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.085

文献信息

• Synthetic Access to 2-Amido-5-aryl-8-methoxy-triazolopyridineand 2-Amido-5-morpholino-8-methoxy-triazolopyridine Derivativesas Potential Inhibitors of the Adenosine Receptor Subtypes
  作者：Matthias Nettekoven、Bernd Püllmann、Sébastien Schmitt

  DOI：10.1055/s-2003-40874

  日期：2003.8

  Two versatile and complementary synthetic strategies towards 2-amido-5-aryl-8-methoxy-triazolopyridine derivatives and 2-amido-5-morpholino-8-methoxy-triazolopyridine derivatives in five steps are presented. The key step in each synthetic route can be constituted as the formation of the respective triazolopyridine derivative precursors in 78% and 57% yield, respectively, through an intermediately formed 4H-[1,2,4]oxadiazol-5-one. The final Suzuki coupling/amidation allowed the straightforward access to the desired triazolopyridine derivatives which have not been described previously. Notably, these triazolopyridine-scaffold bears three vectors of diversity which offer maximum flexibility in design and combinatorial synthesis of molecules with a potentially useful inhibitory activity towards adenosine receptor subtypes.

  本文介绍了两种多功能且互补的合成策略，通过五个步骤制备2-酰胺基-5-芳基-8-甲氧基三唑并吡啶衍生物和2-酰胺基-5-吗啉基-8-甲氧基三唑并吡啶衍生物。每条合成路径的关键步骤是通过中间生成的4H-[1,2,4]二唑-5-酮，分别以78%和57%的产率形成各自的三唑并吡啶衍生物前体。最终的铃木偶联/酰胺化反应使得可以直接获得之前未曾报道过的目标三唑并吡啶衍生物。值得注意的是，这些三唑并吡啶骨架具有三个多样性向量，为设计和组合合成具有潜在阻断腺苷受体亚型活性分子的合成提供了最大的灵活性。
• An efficient coupling of N-tosylhydrazones with 2-halopyridines: synthesis of 2-α-styrylpyridines endowed with antitumor activity
  作者：Marie Lawson、Abdallah Hamze、Jean-François Peyrat、Jérôme Bignon、Joelle Dubois、Jean-Daniel Brion、Mouad Alami

  DOI：10.1039/c3ob40263k

  日期：——

  The synthesis of 2-α-styrylpyridines has been carried out by using the coupling of polyoxygenated N-tosylhydrazones with various 2-halopyridines. We demonstrated that the use of a catalytic amount of PdCl2(MeCN)2 in combination with a bidentate ferrocene DPPF or a monodentate alkyl phosphine tBu2MeP-HBF4 constitutes an efficient protocol for this coupling, providing 2-α-styrylpyridines 2 in satisfactory to good yields. Among several polyoxygenated derivatives 2 evaluated, compound 2aa was found to exhibit excellent antiproliferative and antimitotic activities comparable to that of the reference compound isoCA-4.

  通过利用多氧化的N-对甲苯磺酰腙与各种2-卤代吡啶的偶联反应，已经实现了2-α-苯乙烯基吡啶的合成。我们证明了使用催化量的PdCl2(MeCN)2配合双齿的二茂铁基DPPF或单齿的烷基膦tBu2MeP-HBF4构成了一种高效的偶联反应方案，能够提供令人满意的至良好的产率的2-α-苯乙烯基吡啶2。在评估的几个多氧化衍生物2中，化合物2aa被发现具有与参考化合物isoCA-4相媲美的优异的抗增殖和抗有丝分裂活性。
• Synthesis of novel poly(dithienylpyridines)Electronic supplementary information (ESI) available: further experimental details. See http://www.rsc.org/suppdata/jm/b2/b201229d/
  作者：Glen M. Chapman、Stephen P. Stanforth、Rory Berridge、Cristina Pozo-Gonzalo、Peter J. Skabara

  DOI：10.1039/b201229d

  日期：2002.7.26

  This paper describes the chemical and electrochemical synthesis of novel copolymers of thiophene and pyridine. Di-iodination of 3-hydroxypyridine 12 followed by O-substitution gave a series of ethers 14b–d and esters/carbamates 15a–d which were reacted with the stannylated bithiophene derivative 17 in a Stille cross-coupling reaction yielding poly (1b–d) and poly (2a–d) respectively. These chemical polymerisation reactions generally resulted in highly insoluble materials which were difficult to characterise. Ethers 14b–d and esters/carbamates 15a–d gave O-substituted 3-hydroxy-2,6-di(2-thienyl)pyridines 1b–d and 2a–d respectively in Stille cross-coupling reactions with the stannylated thiophene 16. Ethers 1b–d underwent electrochemical polymerisation allowing the synthesis of O-alkylated polymers, poly (1b–d), with electrochemical band-gaps of 1.4 to 1.6 eV. In contrast, the esters/carbamates 2a–d could not be electropolymerised.

  本文描述了噻吩和吡啶新型共聚物的化学和电化学合成。对3-羟基吡啶12进行双碘化后，通过O-取代反应得到了系列醚14b–d和酯/氨基甲酸酯15a–d，这些化合物与锡基双噻吩衍生物17在Stille交叉偶联反应中反应，分别生成聚合物poly (1b–d)和poly (2a–d)。这些化学聚合反应通常导致高不溶性材料，难以表征。醚14b–d和酯/氨基甲酸酯15a–d在与锡基噻吩16的Stille交叉偶联反应中分别生成O-取代的3-羟基-2,6-二(2-噻吩基)吡啶1b–d和2a–d。醚1b–d进行了电化学聚合，从而合成了O-烷基化聚合物poly (1b–d)，其电化学带隙为1.4至1.6 eV。相比之下，酯/氨基甲酸酯2a–d无法进行电聚合。
• Thiophene-imidazopyridines
  申请人：4SC AG

  公开号：EP2017277A1

  公开（公告）日：2009-01-21

  The invention relates to thiophene-imidazopyridine compounds according to formula (I), wherein the substituents and symbols are as defined in the description. The compounds are inhibitors of PIk1.

  该发明涉及按照公式(I)的噻吩-咪唑吡啶化合物，其中取代基和符号如描述中所定义。这些化合物是PIk1的抑制剂。
• AMINOTRIAZOLOPYRIDINES, COMPOSITIONS THEREOF, AND METHODS OF TREATMENT THEREWITH
  申请人：Bahmanyar Sogole

  公开号：US20100093698A1

  公开（公告）日：2010-04-15

  Provided herein are Heteroaryl Compounds of formula (I): wherein R 1 and R 2 are as defined herein, compositions comprising an effective amount of a Heteroaryl Compound and methods for treating or preventing inflammatory conditions or cancer, and conditions treatable or preventable by inhibition of a kinase or a kinase pathway comprising administering an effective amount of a Heteroaryl Compound to a subject in need thereof.

  本文提供了公式（I）的杂环芳基化合物：其中R1和R2如本文所定义，包含有效量杂环芳基化合物的组合物，以及用于治疗或预防炎症性疾病或癌症的方法，以及通过抑制激酶或激酶途径治疗或预防的疾病，包括向需要的受试者施用有效量杂环芳基化合物。