3-bromo-5-phenylpyridin-2(1H)-one | 1357588-92-1

• 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: 3-bromo-5-phenylpyridin-2(1H)-one
• 英文别名: 3-bromo-5-(phenyl)-2(1H)-pyridinone；3-bromo-5-phenyl-1H-pyridin-2-one
• CAS: 1357588-92-1
• 化学式: C₁₁H₈BrNO
• 分子量: 250.095
• InChiKey: FWFVXNMDNGNLNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氨基-3-溴-5-苯基吡啶 在 吡啶 、 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 2.0h， 以87%的产率得到3-bromo-5-phenylpyridin-2(1H)-one
  参考文献：
  名称：

  A facile synthesis of 3,5-halo and aryl 1H-pyridin-2-ones from pyridinium N-(pyridin-2-yl)aminide

  摘要：

  The synthesis of halogenated and arylated 1H-pyridin-2-ones starting from pyridinium N-(pyridin-2-yl)aminides is described. The synthetic pathway involves the reaction of pyridinium N-(5-bromopyridin-2-yl)aminide, N-(3-bromo-5-chloropyridin-2-yl)aminide or N-(3,5-dibromopyridin-2-yl)aminide with different boronic acids to afford monosubstituted and disubstituted aminides in good yields. An additional bromination in the 3-position of N-(5-arylpyridin-2-yl)aminides was performed. Finally, reduction of the N-N bond followed by the reaction of the corresponding 2-aminopyridines with sodium nitrite/sulfuric acid in water yields 3,5-disubstituted 1H-pyridin-2-ones in good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.065

文献信息

• HETEROCYCLIC COMPOUND AND USE THEREOF
  申请人：Taniguchi Takahiko

  公开号：US20130137675A1

  公开（公告）日：2013-05-30

  The present invention aims to provide a compound having a PDE inhibitory action and useful as a medicament for the prophylaxis or treatment of schizophrenia and the like. A compound represented by the formula (1 x ): wherein each symbol is as described in the DESCRIPTION, or the formula (1): W 1 —W 2 (1) wherein each symbol is as described in the DESCRIPTION, or a salt thereof.

  本发明旨在提供一种具有PDE抑制作用并且用作预防或治疗精神分裂症等疾病的药物的化合物。 由式（1）表示的化合物： 其中每个符号如描述中所述，或式（1）： W1-W2（1） 其中每个符号如描述中所述， 或其盐。
• Protecting Group‐Controlled Regioselective Synthesis for Unsymmetrical 3,5‐Disubstituted Pyridones
  作者：Yong‐Ju Kwon、Won‐Suk Kim

  DOI：10.1002/adsc.202101514

  日期：2022.4.12

  excellent regioselectivity. A one-pot synthesis of unsymmetrical 3,5-diaryl-2-pyridones starting from 3,5-dibromo-2-silyloxypyridine was conducted to demonstrate the practical convenience. Further functionalization onto the remaining bromine group, such as transition metal-catalyzed C−C and C−N bond-forming reactions and retro-Brook rearrangement for C−Si bond formation, was accomplished for synthesis of

  已经研究了保护基团控制的 3,5-二溴-2-吡啶酮的区域选择性功能化以制备不对称的 3,5-二取代 2-吡啶酮。Suzuki-Miyaura 反应中使用庞大的二叔丁基（异丁基）甲硅烷基 (BIBS) 基团进行 C5 区域选择性芳基化。同时，p-甲苯磺酰基 (Ts) 基团用于最大化 C3 选择性卤素-锂交换，采用流动化学。大部分反应进行得很好，产率在 76% 到 95% 之间，具有优异的区域选择性。以 3,5-二溴-2-甲硅烷氧基吡啶为原料，对不对称 3,5-二芳基-2-吡啶酮进行一锅合成，以证明其实用性。对剩余溴基团的进一步功能化，例如过渡金属催化的 C-C 和 C-N 键形成反应和用于 C-Si 键形成的逆布鲁克重排，用于合成生物学相关的 3,5-二取代 2 -吡啶酮。最后，通常用于充血性心力衰竭的氨力农和米力农由 3,5-二溴-2-吡啶酮分三步合成，总收率分别为 41% 和 56%。
• HETEROCYCLIC COMPOUND AND USE THEREOF INHIBITOR OF PHOSPHODIESTERASE 10A
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2604597B1

  公开（公告）日：2017-01-04
• US9150588B2
  申请人：——

  公开号：US9150588B2

  公开（公告）日：2015-10-06
• A facile synthesis of 3,5-halo and aryl 1H-pyridin-2-ones from pyridinium N-(pyridin-2-yl)aminide
  作者：Fabiana Filace、David Sucunza、M. Luisa Izquierdo、Carolina Burgos、Julio Alvarez-Builla

  DOI：10.1016/j.tet.2013.05.065

  日期：2013.7

  The synthesis of halogenated and arylated 1H-pyridin-2-ones starting from pyridinium N-(pyridin-2-yl)aminides is described. The synthetic pathway involves the reaction of pyridinium N-(5-bromopyridin-2-yl)aminide, N-(3-bromo-5-chloropyridin-2-yl)aminide or N-(3,5-dibromopyridin-2-yl)aminide with different boronic acids to afford monosubstituted and disubstituted aminides in good yields. An additional bromination in the 3-position of N-(5-arylpyridin-2-yl)aminides was performed. Finally, reduction of the N-N bond followed by the reaction of the corresponding 2-aminopyridines with sodium nitrite/sulfuric acid in water yields 3,5-disubstituted 1H-pyridin-2-ones in good yields. (C) 2013 Elsevier Ltd. All rights reserved.