methyl 4-benzylamino-3-(benzyloxy)picolinate | 1342906-80-2

• 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
• 英文名称: methyl 4-benzylamino-3-(benzyloxy)picolinate
• 英文别名: Methyl 4-(benzylamino)-3-phenylmethoxypyridine-2-carboxylate；methyl 4-(benzylamino)-3-phenylmethoxypyridine-2-carboxylate
• CAS: 1342906-80-2
• 化学式: C₂₁H₂₀N₂O₃
• 分子量: 348.401
• InChiKey: FFTMACUBYNYFKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-羟基-2-吡啶甲酸 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四(三苯基膦)钯 、 硫酸 、 溴 、 sodium formate 、 potassium carbonate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 102.0h， 生成 methyl 4-benzylamino-3-(benzyloxy)picolinate
  参考文献：
  名称：

  Straightforward and efficient synthesis of 3-benzyloxy-4-bromopicolinate ester and 3-benzyloxy-5-bromopicolinate ester, common building blocks for pharmaceuticals and agrochemicals

  摘要：

  A practical and rapid preparation of 3-benzyloxy-4-bromo and 3-benzyloxy-5-bromopicolinate esters 10 and 16 was developed in four steps, respectively, in 38% and 31% overall yield. Then their viability as partners for cross-coupling reactions has been evaluated in Suzuki-Miyaura, Hartwig-Buchwald, and Sonogashira reactions to synthesize biologically relevant targets. The preparation of these two highly functionalizable pyridines 10 and 16 has been never described to date in the literature and could be used as common building block for the preparation of several biologically active compounds or agrochemical products. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.024

文献信息

• Straightforward and efficient synthesis of 3-benzyloxy-4-bromopicolinate ester and 3-benzyloxy-5-bromopicolinate ester, common building blocks for pharmaceuticals and agrochemicals
  作者：Tristan Verdelet、Guillaume Mercey、Nobi Correa、Ludovic Jean、Pierre-Yves Renard

  DOI：10.1016/j.tet.2011.09.024

  日期：2011.11

  A practical and rapid preparation of 3-benzyloxy-4-bromo and 3-benzyloxy-5-bromopicolinate esters 10 and 16 was developed in four steps, respectively, in 38% and 31% overall yield. Then their viability as partners for cross-coupling reactions has been evaluated in Suzuki-Miyaura, Hartwig-Buchwald, and Sonogashira reactions to synthesize biologically relevant targets. The preparation of these two highly functionalizable pyridines 10 and 16 has been never described to date in the literature and could be used as common building block for the preparation of several biologically active compounds or agrochemical products. (C) 2011 Elsevier Ltd. All rights reserved.