1-(6-bromopyridin-2-yl)-1H-indazole | 1160434-66-1

• 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: 1-(6-bromopyridin-2-yl)-1H-indazole
• 英文别名: 1-(6-Bromopyridin-2-yl)indazole
• CAS: 1160434-66-1
• 化学式: C₁₂H₈BrN₃
• 分子量: 274.12
• InChiKey: VNFOPNVKMANNSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  吡唑 、 1-(6-bromopyridin-2-yl)-1H-indazole 在 sodium hydride 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 122.0h， 以46%的产率得到2-(indazol-1-yl)-6-(pyrazol-2-yl)pyridine
  参考文献：
  名称：

  Unexpected product distributions in the synthesis of 2,6-bis-(indazolyl)pyridine and 2-(pyrazol-1-yl)-6-(indazolyl)pyridine

  摘要：

  Reaction of 2-bromopyridine with 2 equiv of sodium indazolide in diglyme at 140 degrees C affords 2,6-bis-(indazol-1-yl)pyridine and 2-(indazol-1-yl)-6-(indazol-2-yl)pyridine in purified yields of 24% and 68% respectively. A similar reaction, using 1 equiv of sodium inclazolide at 70 degrees C, gives a low-yield mixture of 2-(indazol-1-yl)-6-bromopyridine and 2-(indazol-2-yl)-6-bromopyridine. Both these intermediates are transformed into 2-(pyrazol-1-yl)-6-(indazol-1-yl)pyridine and 2,6-di(pyrazol-1-yl)pyridine upon treatment with I equiv of sodium pyrazolide in diglyme at 140 degrees C. These observations imply that the indazolyl group is a leaving group comparable to a bromo substituent under nucleophilic attack by pyrazolide or indazolide ions under these conditions. No reaction was observed between 2-(pyrazol-1-yl)-6-bromopyridine and 1 equiv of sodium inclazolide under the same conditions. A single crystal structure of its iron(II) complex confirmed the regiochemistry of 2,6-bis-(indazol-1-yl)pyridine, and revealed significant conformational flexibility in the distal ligand indazolyl groups. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.035
• 作为产物：
  描述：

  2,6-二溴吡啶 、 吲唑 在 copper(l) iodide 、 四甲基乙二胺 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.5h， 以41%的产率得到1-(6-bromopyridin-2-yl)-1H-indazole
  参考文献：
  名称：

  2,6-二溴吡啶与胺的选择性形成CN键反应

  摘要：

  通过使用选择性铜催化的 2,6-二溴吡啶和一系列胺之间的 C-N 键形成反应，开发了一种实用且有效的合成 6-取代 2-溴吡啶化合物的方案。该方案的主要优点是完全控制吡啶溴原子对 C-N 交叉偶联反应的选择性。不对称的2,6-二取代吡啶桥化合物由于其制备复杂，很少有报道合成。尽管如此，通过使用这种铜催化偶联方法，已经通过两步成功制备了一系列新的这些不对称化合物。

  DOI：

  10.1002/ejoc.201402619

文献信息

• Metal-free site-selective C–N bond-forming reaction of polyhalogenated pyridines and pyrimidines
  作者：Lei Wang、Ning Liu、Bin Dai

  DOI：10.1039/c5ra18653f

  日期：——

  of the pyridine ring to generate monosubstituted halogenated pyridines with high selectivities. Different halogen atoms at various positions were produced by the pyridine ring that performed well under mild conditions. Halogenated pyrimidines underwent highly selective coupling at the chloride group with a wide range of amines having broad substrate applicability and moderate to good yields. The selectivity

  本文提出了一种多金属的方法，用于多位卤代吡啶和嘧啶的高位点选择性C–N键形成反应。当从吡啶环变为嘧啶环时，优选的偶联位点可从带有N-杂环的氟基团调节至氯基团。各种各样的卤代吡啶优先与吡啶环氟原子上的胺反应，生成具有高选择性的单取代卤代吡啶。吡啶环在不同位置产生了不同的卤素原子，这些吡啶环在温和的条件下表现良好。卤代嘧啶在氯化物基团上与多种胺进行高度选择性的偶联，这些胺具有广泛的底物适用性并且产率中等至良好。氮环的邻位。该反应容纳了广泛的卤代基团。因此，产生了大量的氯，溴，碘和氟吡啶，它们对于有机合成具有广泛的用途。
• Unexpected product distributions in the synthesis of 2,6-bis-(indazolyl)pyridine and 2-(pyrazol-1-yl)-6-(indazolyl)pyridine
  作者：Ruth Pritchard、Colin A. Kilner、Malcolm A. Halcrow

  DOI：10.1016/j.tetlet.2009.03.035

  日期：2009.5

  Reaction of 2-bromopyridine with 2 equiv of sodium indazolide in diglyme at 140 degrees C affords 2,6-bis-(indazol-1-yl)pyridine and 2-(indazol-1-yl)-6-(indazol-2-yl)pyridine in purified yields of 24% and 68% respectively. A similar reaction, using 1 equiv of sodium inclazolide at 70 degrees C, gives a low-yield mixture of 2-(indazol-1-yl)-6-bromopyridine and 2-(indazol-2-yl)-6-bromopyridine. Both these intermediates are transformed into 2-(pyrazol-1-yl)-6-(indazol-1-yl)pyridine and 2,6-di(pyrazol-1-yl)pyridine upon treatment with I equiv of sodium pyrazolide in diglyme at 140 degrees C. These observations imply that the indazolyl group is a leaving group comparable to a bromo substituent under nucleophilic attack by pyrazolide or indazolide ions under these conditions. No reaction was observed between 2-(pyrazol-1-yl)-6-bromopyridine and 1 equiv of sodium inclazolide under the same conditions. A single crystal structure of its iron(II) complex confirmed the regiochemistry of 2,6-bis-(indazol-1-yl)pyridine, and revealed significant conformational flexibility in the distal ligand indazolyl groups. (C) 2009 Elsevier Ltd. All rights reserved.
• Selective C-N Bond-Forming Reaction of 2,6-Dibromopyridine with Amines
  作者：Lei Wang、Ning Liu、Bin Dai、Hengcai Hu

  DOI：10.1002/ejoc.201402619

  日期：2014.10

  A practical and efficient protocol for the syntheses of 6-substituted 2-bromopyridine compounds has been developed by using a selective copper-catalyzed C–N bond-forming reaction between 2,6-dibromopyridine and a range of amines. The major advantage of this protocol is the complete control of selectivity of the pyridine bromine atom for the C–N cross-coupling reaction. There are few reported syntheses

  通过使用选择性铜催化的 2,6-二溴吡啶和一系列胺之间的 C-N 键形成反应，开发了一种实用且有效的合成 6-取代 2-溴吡啶化合物的方案。该方案的主要优点是完全控制吡啶溴原子对 C-N 交叉偶联反应的选择性。不对称的2,6-二取代吡啶桥化合物由于其制备复杂，很少有报道合成。尽管如此，通过使用这种铜催化偶联方法，已经通过两步成功制备了一系列新的这些不对称化合物。