N-(pyridin-3-yl)furan-2-carboxamide | 36880-64-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(pyridin-3-yl)furan-2-carboxamide
• 英文别名: 3-(2'-furoyl)aminopyridine；furan-2-carboxylic acid pyridin-3-ylamide；N-[3]pyridyl-furan-2-carboxamide；N-[3]Pyridyl-furan-2-carbamid；N-<3>Pyridyl-furan-2-carbonsaeureamid；2-Furancarboxamide, N-3-pyridinyl-；N-pyridin-3-ylfuran-2-carboxamide
• CAS: 36880-64-5
• 化学式: C₁₀H₈N₂O₂
• mdl: MFCD00804856
• 分子量: 188.186
• InChiKey: KNLDTIUTQAWHPW-UHFFFAOYSA-N

物化性质

• 熔点：
  142-143 °C
• 沸点：
  237.3±15.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为产物：
  描述：

  3-氯吡啶 、 糠酰胺 在 potassium phosphate 、 2-二叔丁基膦-2′,4′,6′-三异丙基-3,6-二甲氧基-1,1′-联苯 、 水 、 palladium diacetate 作用下， 以 叔丁醇 为溶剂， 反应 1.5h， 以96%的产率得到N-(pyridin-3-yl)furan-2-carboxamide
  参考文献：
  名称：

  An efficient system for the Pd-catalyzed cross-coupling of amides and aryl chlorides

  摘要：

  A catalyst based on a new biarylphosphine ligand (3) for the Pd-catalyzed cross-coupling reactions of amides and aryl chlorides is described. This system shows the highest turnover frequencies reported to date for these reactions, especially for aryl chloride substrates bearing an ortho substituent. An array of amides and aryl chlorides were successfully reacted in good to excellent yields. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.096

文献信息

• 3-Amino- and 3-acylamido-2-phosphonopyridines: synthesis by Pd-catalyzed P–C coupling, structure and conversion to pyrido[b]-anellated PC–N heterocycles
  作者：Mohamed Shaker S. Adam、Olaf Kühl、Markus K. Kindermann、Joachim W. Heinicke、Peter G. Jones

  DOI：10.1016/j.tet.2008.06.010

  日期：2008.8

  4a to the novel pyrido[b]-anellated 1,3-azaphosphole 5a. Reaction of amidophosphonates 2b–f with LiAlH4 did not result in the expected reductive cyclization, as shown by closely related anilido-2-phosphonates, but led to product mixtures containing N-secondary 3-amino-2-phosphinopyridines 3b–f as the main or major component. The conversion of 3b,d,e with DMFA to 5b,d,e provides first examples of N-substituted

  钯催化的3-氨基和3-酰氨基-2-溴吡啶的交叉偶联1A - ˚F与亚磷酸三乙酯的允许3-氨基和3-酰氨吡啶-2-膦酸二酯的合成2A - ˚F，而镍催化剂虽然可以提供相关的苯胺基-2-膦酸酯，但被证明是无活性的。用LiAlH 4还原氨基膦酸酯2a，得到3-氨基-2-膦基吡啶（3a），将其与二甲基甲酰胺二甲基乙缩醛（DMFA）经由磷烯烃中间体4a环缩合为新型吡啶并[ b ]取代的1,3-氮杂磷腈5a。。amidophosphonates的反应2B - ˚F用的LiAlH 4并没有导致在预期还原环合，如由密切相关的酰苯胺-2-膦示出，但导致了含有产物的混合物Ñ -secondary 3-氨基-2- phosphinopyridines 3B - ˚F作为主要或主要组成部分。的转化率图3b，d，ê用DMFA至图5b，d，È提供的第一实施例ñ -取代的吡啶并[ b ] -anellated azap
• Mndshojan et al., Doklady Akademii Nauk Armyanskoi SSR, 1953, vol. 17, p. 119,122
  作者：Mndshojan et al.

  DOI：——

  日期：——
• An efficient system for the Pd-catalyzed cross-coupling of amides and aryl chlorides
  作者：Brett P. Fors、Karin Dooleweerdt、Qingle Zeng、Stephen L. Buchwald

  DOI：10.1016/j.tet.2009.04.096

  日期：2009.8

  A catalyst based on a new biarylphosphine ligand (3) for the Pd-catalyzed cross-coupling reactions of amides and aryl chlorides is described. This system shows the highest turnover frequencies reported to date for these reactions, especially for aryl chloride substrates bearing an ortho substituent. An array of amides and aryl chlorides were successfully reacted in good to excellent yields. (C) 2009 Elsevier Ltd. All rights reserved.