N-(2-fluoropyridin-4-yl)pyridin-3-amine | 1239969-47-1

• 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: N-(2-fluoropyridin-4-yl)pyridin-3-amine
• 英文别名: 2-fluoro-N-pyridin-3-ylpyridin-4-amine
• CAS: 1239969-47-1
• 化学式: C₁₀H₈FN₃
• 分子量: 189.192
• InChiKey: CPYRATIVWYSHRS-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：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氨基吡啶 、 2-氟-4-碘吡啶 在 palladium diacetate 、 potassium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以79%的产率得到N-(2-fluoropyridin-4-yl)pyridin-3-amine
  参考文献：
  名称：

  Selective and Facile Palladium-Catalyzed Amination of 2-Fluoro-4-iodopyridine in the 4-Position under Microwave Conditions

  摘要：

  报道了2-氟-4-碘吡啶与芳香胺的选择性C-N交叉耦合反应。与传统取代反应中C-N键在2-位形成（例如2,4-二氯吡啶）不同，Buchwald-Hartwig交叉耦合反应被发现是互补且仅限于4-位的。反应通常在微波辐射下进行，仅需30分钟。这些条件下还使得所需碱的量减少到3.5当量，相比之下，传统协议中需要20当量。此外，使用温和的碱碳酸钾即可，且在所有情况下，采用简单的Pd(OAc)2/BINAP体系均能获得良好的耦合产物收率。

  DOI：

  10.1055/s-0029-1219940

文献信息

• Metal assisted synthesis of mono and diamino substituted pyridines
  作者：Moumita Koley、Michael Schnürch、Marko D. Mihovilovic

  DOI：10.1016/j.tet.2011.04.060

  日期：2011.6

  A microwave assisted Buchwald-Hartwig amination protocol is reported for a series of dihalopyridine precursors. Using this procedure, selective substitution of one halogen by aryl or alkylamines is possible in very short time, usually 30 min. Mild base (K(2)CO(3)) can be used successfully, which broadens the substrate scope. The second halogen can then be substituted using alkylamines under nucleophilic substitution condition or via a Suzuki-Miyaura cross-coupling reaction. The target compounds are potential inducers of cardiomyogenesis as innovative approach in regenerative medicine. (C) 2011 Elsevier Ltd. All rights reserved.
• Selective and Facile Palladium-Catalyzed Amination of 2-Fluoro-4-iodopyridine in the 4-Position under Microwave Conditions
  作者：Marko Mihovilovic、Moumita Koley、Michael Schnürch

  DOI：10.1055/s-0029-1219940

  日期：2010.6

  The selective C-N cross-coupling of 2-fluoro-4-iodopyr­idine with aromatic amines is reported. In contrast to conventional substitutions where C-N bond formation takes place at the 2-position (e.g., 2,4-dichloropyridine), the Buchwald-Hartwig cross-­coupling was found to be complementary and exclusive for the 4-position. Reactions were carried out under microwave irradiation typically within 30 minutes. These conditions also allowed a decrease in the amount of base required to 3.5 equivalents compared to 20 equivalents in established protocols. Additionally, use of potassium carbonate as a mild base was sufficient, and good yields of the coupling products were obtained in all cases with the simple system Pd(OAc)2/BINAP.

  报道了2-氟-4-碘吡啶与芳香胺的选择性C-N交叉耦合反应。与传统取代反应中C-N键在2-位形成（例如2,4-二氯吡啶）不同，Buchwald-Hartwig交叉耦合反应被发现是互补且仅限于4-位的。反应通常在微波辐射下进行，仅需30分钟。这些条件下还使得所需碱的量减少到3.5当量，相比之下，传统协议中需要20当量。此外，使用温和的碱碳酸钾即可，且在所有情况下，采用简单的Pd(OAc)2/BINAP体系均能获得良好的耦合产物收率。