3-azido-2-bromopyridine | 1212822-03-1

• 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-azido-2-bromopyridine
• 英文别名: 3-azide-2-bromopyridine；3-Azido-2-bromopyridine
• CAS: 1212822-03-1
• 化学式: C₅H₃BrN₄
• 分子量: 199.01
• InChiKey: IUHCKTZHEDFNMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 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：
  27.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-azido-2-bromopyridine 、 1-萘-2-基丙烷-2-酮 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以93%的产率得到2-bromo-3-(5-methyl-4-(naphthalen-2-yl)-1H-1,2,3-triazol-1-yl)pyridine
  参考文献：
  名称：

  乙醇酸介导的有机催化叠氮化物-酮[3 + 2]-环加成反应：完全装饰的1,2,3-三唑的区域选择性高产合成

  摘要：

  烯醇介导的有机催化叠氮化物-酮[3 + 2]-环加成（OrgAKC）反应由多种可烯醇化的丙酮和脱氧安息香素与叠氮化物开发，用于合成完全装饰的1,4-二芳基-5-甲基（烷基） ‐1,2,3-三唑在25°C下保持0.5–6 h时具有极高的选择性，并具有较高的区域选择性。该反应在反应速率，产率，区域选择性，操作简便性以及底物和催化剂的可用性方面具有优异的结果。该反应比以前已知的金属介导反应更具优势。

  DOI：

  10.1002/chem.201405501
• 作为产物：
  描述：

  2-溴-3-氨基吡啶 在 tetrafluoroboric acid 、 sodium nitrite 、 sodium azide 作用下， 以 水 为溶剂， 反应 4.0h， 生成 3-azido-2-bromopyridine
  参考文献：
  名称：

  Synthesis and evaluation of 6-[1-(2-[18F]fluoro-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline for positron emission tomography imaging of the metabotropic glutamate receptor type 1 in brain

  摘要：

  The purpose of this study was to synthesize 6-[1-(2-[F-18]fluoro-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline ([F-18]FPTQ, [F-18]7a) and to evaluate its potential as a positron emission tomography ligand for imaging metabotropic glutamate receptor type 1 (mGluR1) in the rat brain. Compound [F-18]7a was synthesized by [F-18] fluorination of 6-[1-(2-bromo-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl] quinoline (7b) with potassium [F-18] fluoride. At the end of synthesis, 1280-1830 MBq (n = 8) of [F-18]7a was obtained with >98% radiochemical purity and 118-237 GBq/mu mol specific activity using 3300-4000 MBq of [F-18]F . In vitro autoradiography showed that [F-18]7a had high specific binding with mGluR1 in the rat brain. Biodistribution study using a dissection method and small-animal PET showed that [F-18]7a had high uptake in the rat brain. The uptake of radioactivity in the cerebellum was reduced by unlabeled 7a and mGluR1-selective ligand JNJ-16259685 (2), indicating that [F-18]7a had in vivo specific binding with mGluR1. Because of a low amount of radiolabeled metabolite present in the brain, [F-18]7a may have a limiting potential for the in vivo imaging of mGluR1 by PET. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.048

文献信息

• EP1726585
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and evaluation of 6-[1-(2-[18F]fluoro-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline for positron emission tomography imaging of the metabotropic glutamate receptor type 1 in brain
  作者：Masayuki Fujinaga、Tomoteru Yamasaki、Kazunori Kawamura、Katsushi Kumata、Akiko Hatori、Joji Yui、Kazuhiko Yanamoto、Yuichiro Yoshida、Masanao Ogawa、Nobuki Nengaki、Jun Maeda、Toshimitsu Fukumura、Ming-Rong Zhang

  DOI：10.1016/j.bmc.2010.11.048

  日期：2011.1

  The purpose of this study was to synthesize 6-[1-(2-[F-18]fluoro-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline ([F-18]FPTQ, [F-18]7a) and to evaluate its potential as a positron emission tomography ligand for imaging metabotropic glutamate receptor type 1 (mGluR1) in the rat brain. Compound [F-18]7a was synthesized by [F-18] fluorination of 6-[1-(2-bromo-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl] quinoline (7b) with potassium [F-18] fluoride. At the end of synthesis, 1280-1830 MBq (n = 8) of [F-18]7a was obtained with >98% radiochemical purity and 118-237 GBq/mu mol specific activity using 3300-4000 MBq of [F-18]F . In vitro autoradiography showed that [F-18]7a had high specific binding with mGluR1 in the rat brain. Biodistribution study using a dissection method and small-animal PET showed that [F-18]7a had high uptake in the rat brain. The uptake of radioactivity in the cerebellum was reduced by unlabeled 7a and mGluR1-selective ligand JNJ-16259685 (2), indicating that [F-18]7a had in vivo specific binding with mGluR1. Because of a low amount of radiolabeled metabolite present in the brain, [F-18]7a may have a limiting potential for the in vivo imaging of mGluR1 by PET. (C) 2010 Elsevier Ltd. All rights reserved.
• An Enolate-Mediated Organocatalytic Azide-Ketone [3+2]-Cycloaddition Reaction: Regioselective High-Yielding Synthesis of Fully Decorated 1,2,3-Triazoles
  作者：Adluri B. Shashank、S. Karthik、R. Madhavachary、Dhevalapally B. Ramachary

  DOI：10.1002/chem.201405501

  日期：2014.12.15

  An enolate‐mediated organocatalytic azide–ketone [3+2]‐cycloaddition (OrgAKC) reaction of a variety of enolizable arylacetones and deoxybenzoins with aryl azides was developed for the synthesis of fully decorated 1,4‐diaryl‐5‐methyl(alkyl)‐1,2,3‐triazoles in excellent yields with high regioselectivity at 25 °C for 0.5–6 h. This reaction has an excellent outcome with reference to reaction rate, yield

  烯醇介导的有机催化叠氮化物-酮[3 + 2]-环加成（OrgAKC）反应由多种可烯醇化的丙酮和脱氧安息香素与叠氮化物开发，用于合成完全装饰的1,4-二芳基-5-甲基（烷基） ‐1,2,3-三唑在25°C下保持0.5–6 h时具有极高的选择性，并具有较高的区域选择性。该反应在反应速率，产率，区域选择性，操作简便性以及底物和催化剂的可用性方面具有优异的结果。该反应比以前已知的金属介导反应更具优势。