methyl 2-[3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetate | 947688-89-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-[3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetate
• 英文别名: Methyl 2-(3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetate
• CAS: 947688-89-3
• 化学式: C₁₅H₂₂BNO₅
• 分子量: 307.154
• InChiKey: MTUKYQJDGQSQIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-[3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetate 在 4-二甲氨基吡啶 、 双氧水 作用下， 以 二氯甲烷 、 氯苯 为溶剂， 反应 15.5h， 生成 methyl 2-[5-(6,7-dimethoxyquinolin-4-yloxy)-3-methoxypyridin-2-yl]acetate
  参考文献：
  名称：

  Discovery of new quinoline ether inhibitors with high affinity and selectivity for PDGFR tyrosine kinases

  摘要：

  A new series of quinoline ether inhibitors, which potently and selectively inhibit PDGFR tyrosine kinases, is described in this Letter. Compounds 23 and 33 are selective, low nanomolar inhibitors of PDGFR alpha and beta, display good pharmacokinetics in rat and dog and are active in vivo at low doses when given orally twice daily. Further evaluation of these compounds is warranted. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.074
• 作为产物：
  描述：

  5-溴-2-氯-3-甲氧基吡啶 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 三甲基氯硅烷 、 potassium acetate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 10.0h， 生成 methyl 2-[3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetate
  参考文献：
  名称：

  Discovery of new quinoline ether inhibitors with high affinity and selectivity for PDGFR tyrosine kinases

  摘要：

  A new series of quinoline ether inhibitors, which potently and selectively inhibit PDGFR tyrosine kinases, is described in this Letter. Compounds 23 and 33 are selective, low nanomolar inhibitors of PDGFR alpha and beta, display good pharmacokinetics in rat and dog and are active in vivo at low doses when given orally twice daily. Further evaluation of these compounds is warranted. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.074

文献信息

• QUINOLINE DERIVATIVES
  申请人：Jung Frederic Henri

  公开号：US20090076075A1

  公开（公告）日：2009-03-19

  The invention concerns quinoline derivatives of Formula I or a pharmaceutically-acceptable salt thereof, wherein each of X 1 , p, R 1 , q, R 2 , R 3 , R 4 , R 5 Ring A, r and R 6 has any of the meanings defined hereinbefore in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the treatment of cell proliferative disorders.

  这项发明涉及公式I的喹啉衍生物或其药用盐，其中X 1 ，p，R 1 ，q，R 2 ，R 3 ，R 4 ，R 5 ，环A，r和R 6 中的每一个具有在描述中定义的任何含义；它们的制备方法，含有它们的药物组合物以及它们在制造用于治疗细胞增殖紊乱的药物的药物中的使用。
• An efficient large-scale synthesis of alkyl 5-hydroxy-pyridin- and pyrimidin-2-yl acetate
  作者：Rémy Morgentin、Frédéric Jung、Maryannick Lamorlette、Mickaël Maudet、Morgan Ménard、Patrick Plé、Georges Pasquet、Fabrice Renaud

  DOI：10.1016/j.tet.2008.11.064

  日期：2009.1

  of methyl 2-(5-hydroxy-3-methoxypyridin-2-yl)acetate and alkyl 2-(5-hydroxypyrimidin-2-yl)acetate is described. Methodology for an efficient access to 5-hydroxy-pyridin- and pyrimidin-2-yl acetate cores has been developed. Based on the difference in halogen reactivity, 5-bromo-2-chloropyridine and its pyrimidine analogue were functionalized judiciously by SNAr and palladium-catalyzed reactions. The

  描述了2-（5-羟基-3-甲氧基吡啶-2-基）乙酸甲酯和2-（5-羟基嘧啶-2-基）乙酸烷基酯的合成。已经开发出有效获得5-羟基吡啶和乙酸嘧啶-2-基乙酸盐核心的方法。根据卤素反应性的差异，通过S N Ar和钯催化的反应将5-溴-2-氯吡啶及其嘧啶类似物适当地官能化。概述的策略提供了适用于这些化合物大规模合成的高产途径，并为潜在快速获得其他杂环类似物铺平了道路。
• WO2007/99317
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• WO2007/113548
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• WO2007/113565
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