6-溴-3-氯-5-氟-2-吡啶羧酸 | 514798-17-5

• 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: 6-溴-3-氯-5-氟-2-吡啶羧酸
• 中文别名: 6-溴-3-氯-5-氟吡啶甲酸
• 英文名称: 6-bromo-3-chloro-5-fluoro-2-pyridinecarboxylic acid
• 英文别名: 6-Bromo-3-chloro-5-fluoropicolinic acid；6-bromo-3-chloro-5-fluoropyridine-2-carboxylic acid
• CAS: 514798-17-5
• 化学式: C₆H₂BrClFNO₂
• 分子量: 254.443
• InChiKey: BCHIHNFJSXHACA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-溴-3-氯-5-氟-2-吡啶羧酸 在 三甲基氯硅烷 、 硫酸 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 21.0h， 生成 methyl 3-chloro-5-fluoro-6-iodo-2-pyridinecarboxylate
  参考文献：
  名称：

  Creating Structural Manifolds from a Common Precursor: Basicity Gradient-Driven Isomerization of Halopyridines

  摘要：

  5-Chloro-2,3-difluoropyridine, an intermediate in the manufacturing process of an industrial pesticide, can be hydrolyzed to 5-chloro-3-fluoro-2H-pyridinone and the latter converted into 2,5-dichloro-3-fluoropyridine (1a), 2-bromo-5chloro-3-fluoropyridine (1b), 5-chloro-3-fluoro-2-iodopyridine (1c) and 3-chloro-5-fluoropyridine (1d). Consecutive treatment of these four substrates with lithium diisopropylamide and carbon dioxide or lithium diisopropylamide and iodine affords the corresponding 4-pyridinecarboxylic acids 2 and 4-iodopyridines 3, respectively. Amide-promoted deprotonation of such 4-iodopyridines 3 triggers an isomerization in which lithium and iodine change places. The resulting species can be trapped with carbon dioxide to give the acids 5a-c or neutralized to give the halopyridines 4a-c. The iodopyridines 4a and 4b can be converted into the acids 6a and 6b, the latter product leading also to the congeners 6c and 6d. The diiodopyridine 4c provides an entry to the halopyridine 4d, which at the same time may act as the precursor to the acid 5d, the acid 7 or the bisacid 8. Finally, the acid 9 is accessible from either one of the 5-chloro-3-fluoro-2-halopyridines 1b and 1c. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200212)2002:24<4174::aid-ejoc4174>3.0.co;2-6
• 作为产物：
  描述：

  2-溴-3-氟-5-氯吡啶 在 2,2,6,6-四甲基哌啶 、 正丁基锂 、 异丙基氯化镁 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.25h， 生成 6-溴-3-氯-5-氟-2-吡啶羧酸
  参考文献：
  名称：

  Creating Structural Manifolds from a Common Precursor: Basicity Gradient-Driven Isomerization of Halopyridines

  摘要：

  5-Chloro-2,3-difluoropyridine, an intermediate in the manufacturing process of an industrial pesticide, can be hydrolyzed to 5-chloro-3-fluoro-2H-pyridinone and the latter converted into 2,5-dichloro-3-fluoropyridine (1a), 2-bromo-5chloro-3-fluoropyridine (1b), 5-chloro-3-fluoro-2-iodopyridine (1c) and 3-chloro-5-fluoropyridine (1d). Consecutive treatment of these four substrates with lithium diisopropylamide and carbon dioxide or lithium diisopropylamide and iodine affords the corresponding 4-pyridinecarboxylic acids 2 and 4-iodopyridines 3, respectively. Amide-promoted deprotonation of such 4-iodopyridines 3 triggers an isomerization in which lithium and iodine change places. The resulting species can be trapped with carbon dioxide to give the acids 5a-c or neutralized to give the halopyridines 4a-c. The iodopyridines 4a and 4b can be converted into the acids 6a and 6b, the latter product leading also to the congeners 6c and 6d. The diiodopyridine 4c provides an entry to the halopyridine 4d, which at the same time may act as the precursor to the acid 5d, the acid 7 or the bisacid 8. Finally, the acid 9 is accessible from either one of the 5-chloro-3-fluoro-2-halopyridines 1b and 1c. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200212)2002:24<4174::aid-ejoc4174>3.0.co;2-6

文献信息

• [EN] ALKYNYL ALCOHOLS AND METHODS OF USE<br/>[FR] ALCOOLS ALCYNYLIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015025026A1

  公开（公告）日：2015-02-26

  The invention relates to compounds of Formula (0): wherein A1-A8, R4 and R5 each has the meaning as described herein. Compounds of Formula (0) and pharmaceutical compositions thereof are useful in the treatment of diseases and disorders in which undesired or over-activation of NF-kB signaling is observed.

  该发明涉及以下式的化合物（0）：其中A1-A8，R4和R5分别具有如本文所述的含义。该式（0）的化合物及其药物组合物在治疗观察到NF-kB信号不良或过度激活的疾病和紊乱中是有用的。
• ALKYNYL ALCOHOLS AND METHODS OF USE
  申请人：F.Hoffmann-La Roche AG

  公开号：EP3036229A1

  公开（公告）日：2016-06-29
• WO2023/169984
  申请人：——

  公开号：——

  公开（公告）日：——
• Creating Structural Manifolds from a Common Precursor: Basicity Gradient-Driven Isomerization of Halopyridines
  作者：Manfred Schlosser、Carla Bobbio

  DOI：10.1002/1099-0690(200212)2002:24<4174::aid-ejoc4174>3.0.co;2-6

  日期：2002.12

  5-Chloro-2,3-difluoropyridine, an intermediate in the manufacturing process of an industrial pesticide, can be hydrolyzed to 5-chloro-3-fluoro-2H-pyridinone and the latter converted into 2,5-dichloro-3-fluoropyridine (1a), 2-bromo-5chloro-3-fluoropyridine (1b), 5-chloro-3-fluoro-2-iodopyridine (1c) and 3-chloro-5-fluoropyridine (1d). Consecutive treatment of these four substrates with lithium diisopropylamide and carbon dioxide or lithium diisopropylamide and iodine affords the corresponding 4-pyridinecarboxylic acids 2 and 4-iodopyridines 3, respectively. Amide-promoted deprotonation of such 4-iodopyridines 3 triggers an isomerization in which lithium and iodine change places. The resulting species can be trapped with carbon dioxide to give the acids 5a-c or neutralized to give the halopyridines 4a-c. The iodopyridines 4a and 4b can be converted into the acids 6a and 6b, the latter product leading also to the congeners 6c and 6d. The diiodopyridine 4c provides an entry to the halopyridine 4d, which at the same time may act as the precursor to the acid 5d, the acid 7 or the bisacid 8. Finally, the acid 9 is accessible from either one of the 5-chloro-3-fluoro-2-halopyridines 1b and 1c. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002).