N-叔-丁基-3-碘-吡啶-4-甲酰胺 | 331969-21-2

• 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
• 中文名称: N-叔-丁基-3-碘-吡啶-4-甲酰胺
• 英文名称: N-(tert-Butyl)-3-iodopyridine-3-carboxamide
• 英文别名: N-(tert-butyl)-3-iodopyridine-4-carboxamide；N-tert-butyl-3-iodopyridine-4-carboxamide
• CAS: 331969-21-2
• 化学式: C₁₀H₁₃IN₂O
• 分子量: 304.131
• InChiKey: SCGDHGAWTIPMDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-叔丁基异烟酰胺 在 碘 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以66%的产率得到N-叔-丁基-3-碘-吡啶-4-甲酰胺
  参考文献：
  名称：

  Deprotonation of pyridine carboxamides using lithium magnesiates bases

  摘要：

  Regioselective deprotonation of N-methyl- and tert-butylpyridine carboxamides using lithium magnesiates bases was achieved at room temperature avoiding nucleophilic addition on the pyridine molecule and auto-condensation of the arylmetal intermediates on the amide group was described. The hydrogen-magnesium exchange was evidenced using H-1 NMR spectroscopy at room temperature and the reactivity of the lithium 2- 3- and 4-carboxamidopyridinylmagnesiates complexes towards electrophiles and in cross-coupling reactions was studied. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.064

文献信息

• Reaction of magnesiated bases on substituted pyridines: deprotonation or 1,4-addition?
  作者：Véronique Bonnet、Florence Mongin、François Trécourt、Guy Quéguiner

  DOI：10.1039/b007270m

  日期：——

  N-(tert-Butyl)pyridine-2-carboxamide (1), N-phenylpyridine-2-carboxamide (7) and 2,2-dimethyl-N-(2-pyridyl)propanamide (18) are readily deprotonated at C3 with a stoichiometric amount of PriMgCl or Bu2Mg in THF under reflux. Subsequent trapping with various electrophiles (deuterated water, aldehydes, iodine and dimethyl disulfide) gives 2,3-disubstituted pyridines carrying a useful carboxylic acid- or amino-derived function at C2. When N-(tert-butyl)pyridine-3-carboxamide (12) and 2,2-dimethyl-N-(3-pyridyl)propanamide (22) are subjected to the same reaction conditions, 1,4-addition to the pyridine ring occurs, giving 4-alkyl derivatives. Starting from N-(tert-butyl)pyridine-4-carboxamide (15), 1,2-addition and deprotonation reactions occur simultaneously.

  N-(叔丁基)pyridine-2-carboxamide (1)、N-苯基pyridine-2-carboxamide (7) 和 2,2-二甲基-N-(2-吡啶基)丙酰胺 (18) 在THF回流条件下，使用化学计量的PriMgCl或Bu2Mg容易地在C3位去质子化。随后与各种电亲体（氘水、醛、碘和二甲基二硫）反应，得到在C2位带有有用的羧酸或氨基衍生基团的2,3-二取代吡啶。当N-(叔丁基)pyridine-3-carboxamide (12) 和2,2-二甲基-N-(3-吡啶基)丙酰胺 (22) 在相同的反应条件下，发生对吡啶环的1,4-加成，生成4-烷基衍生物。从N-(叔丁基)pyridine-4-carboxamide (15) 开始，1,2-加成和去质子化反应同时发生。
• Deprotonation of pyridine carboxamides using lithium magnesiates bases
  作者：Haçan Hawad、Omar Bayh、Christophe Hoarau、Francois Trécourt、Guy Quéguiner、Francis Marsais

  DOI：10.1016/j.tet.2008.01.064

  日期：2008.3

  Regioselective deprotonation of N-methyl- and tert-butylpyridine carboxamides using lithium magnesiates bases was achieved at room temperature avoiding nucleophilic addition on the pyridine molecule and auto-condensation of the arylmetal intermediates on the amide group was described. The hydrogen-magnesium exchange was evidenced using H-1 NMR spectroscopy at room temperature and the reactivity of the lithium 2- 3- and 4-carboxamidopyridinylmagnesiates complexes towards electrophiles and in cross-coupling reactions was studied. (c) 2008 Elsevier Ltd. All rights reserved.

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