2-bromo-3-(methylthio)pyridine | 884863-17-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-bromo-3-(methylthio)pyridine
• 英文别名: 2-bromo-3-methylsulfanylpyridine
• CAS: 884863-17-6
• 化学式: C₆H₆BrNS
• 分子量: 204.09
• InChiKey: QDUBYPZLIZYQNK-UHFFFAOYSA-N

物化性质

• 沸点：
  267.5±25.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-3-(methylthio)pyridine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 溴 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 1.5h， 生成 3-bromo-2-phenylthieno[3,2-b]pyridine
  参考文献：
  名称：

  Regiocontrolled SNAr Reaction on 2,3-Dihalopyridines with NaSMe To Obtain Bromo(methylthio)pyridines as Key Precursors of 3-Halo-2-(hetero)arylthieno[2,3-b]pyridines and Thieno[3,2-b]pyridines

  摘要：

  The synthesis of 3-halo-2-(hetero) arylthieno[2,3-b]pyridines and 3-halo-2-(hetero) arylthieno[3,2-b]pyridines has been performed through a three-step methodology from 3-bromo-2-chloropyridine or 2-bromo-3-fluoropyridine, respectively. The key step of this methodology is the formation of the required bromo(methylthio)pyridines by a regiocontrolled nucleophilic aromatic substitution (SNAr) with sodium methanethiolate (NaSMe). Then, the Sonogashira coupling with (hetero)arylalkynes followed by a halocyclization with bromine or iodine, afforded the expected 3-halo-2-(hetero)arylthienopyridines.

  DOI：

  10.1055/s-0033-1338442
• 作为产物：
  描述：

  3-(甲基硫代)吡啶 在 正丁基锂 、 N,N-二甲基乙醇胺 、 四溴化碳 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 19.0h， 以59%的产率得到2-bromo-3-(methylthio)pyridine
  参考文献：
  名称：

  New efficient access to thieno[3,2-b]pyridine derivatives via regioselective lithiation of 3-methylthiopyridine

  摘要：

  The synthesis of thieno[3,2-b]pyridines was achieved using a three-step process allowing the construction of the thiophenic ring with 17-34% overall yields. The key step was the regioselective lithiation-bromination of the 3-methylthiopyridine induced by BuLi-LiDMAE superbase followed by Sonogashira coupling and halogenocyclization producing the fused heterocycles. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.008

文献信息

• Thiolate-Initiated Synthesis of Dibenzothiophenes from 2,2′-Bis(methylthio)-1,1′-Biaryl Derivatives through Cleavage of Two Carbon–Sulfur Bonds
  作者：Yoshihiro Masuya、Yuki Kawashima、Takuya Kodama、Naoto Chatani、Mamoru Tobisu

  DOI：10.1055/s-0037-1611974

  日期：2019.10

  A catalytic reaction involving the cleavage of two carbon–sulfur bonds in 2,2′-bis(methylthio)-1,1′-biaryl derivatives is reported. This reaction does not require a transition-metal catalyst and is promoted by a thiolate anion. Notably, based on DFT calculations, the product-forming cyclization step is shown to proceed through a concerted nucleophilic aromatic substitution (CSNAr) mechanism.

  报道了涉及裂解 2,2'-双(甲硫基)-1,1'-联芳基衍生物中的两个碳-硫键的催化反应。该反应不需要过渡金属催化剂，并由硫醇盐阴离子促进。值得注意的是，根据 DFT 计算，形成产物的环化步骤显示出通过协同的亲核芳香取代 (CSNAr) 机制进行。
• NEW AZABENZIMIDAZOLE DERIVATIVES
  申请人：HIMMELSBACH Frank

  公开号：US20150025065A1

  公开（公告）日：2015-01-22

  The present invention relates to compounds of general formula I, wherein the group R 1 , R 2 , X and Y are defined as in claim 1 , which have valuable pharmacological properties, in particular bind to the AMP-activated protein kinase (AMPK) and modulate its activity. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.

  本发明涉及一般式I的化合物，其中基团R1、R2、X和Y的定义如权利要求1中所述，具有有价值的药理特性，特别是与AMP-活化蛋白激酶（AMPK）结合并调节其活性。这些化合物适用于治疗和预防受该受体影响的疾病，如代谢性疾病，特别是2型糖尿病。
• [EN] HETEROARYL INHIBITORS OF PAD4<br/>[FR] INHIBITEURS HÉTÉROARYLES DE PAD4
  申请人：PADLOCK THERAPEUTICS INC

  公开号：WO2017147102A1

  公开（公告）日：2017-08-31

  The present invention provides compounds useful as inhibitors of PAD4, compositions thereof, and methods of treating PAD4-related disorders.

  本发明提供了作为PAD4抑制剂有用的化合物，其组成物，以及治疗PAD4相关疾病的方法。
• [EN] COMPOUNDS FOR THE TREATMENT OF PARAMOXYVIRUS VIRAL INFECTIONS<br/>[FR] COMPOSÉS POUR LE TRAITEMENT D'INFECTIONS VIRALES PAR PARAMYXOVIRUS
  申请人：ALIOS BIOPHARMA INC

  公开号：WO2014031784A1

  公开（公告）日：2014-02-27

  Disclosed herein are new antiviral compounds, together with pharmaceutical compositions that include one or more antiviral compounds, and methods of synthesizing the same. Also disclosed herein are methods of ameliorating and/or treating a paramyxovirus viral infection with one or more small molecule compounds. Examples of paramyxovirus infection include an infection caused by human respiratory syncytial virus (RSV).

  本文披露了新的抗病毒化合物，以及包含一种或多种抗病毒化合物的药物组合物，并且揭示了合成这些化合物的方法。本文还披露了利用一种或多种小分子化合物改善和/或治疗副黏病毒病毒感染的方法。副黏病毒感染的例子包括由人类呼吸道合胞病毒（RSV）引起的感染。
• Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzothiophenes via the Annulation of Aryl Sulfides with Alkynes
  作者：Yoshihiro Masuya、Mamoru Tobisu、Naoto Chatani

  DOI：10.1021/acs.orglett.6b02055

  日期：2016.9.2

  A new method has been developed for the synthesis of 2,3-disubstituted benzothiophenes involving the palladium-catalyzed annulation of aryl sulfides with alkynes. This convergent approach exhibited good functional group tolerance, providing rapid access to a diverse array of derivatives from simple, readily available starting materials. This protocol can also be used to synthesize 2-silyl-substituted

  已开发出一种新的合成2,3-二取代的苯并噻吩的方法，该方法涉及钯催化的芳基硫醚与炔烃的环化反应。这种趋同的方法表现出良好的官能团耐受性，可从简单，容易获得的起始原料中快速获得各种衍生物。该协议也可用于合成2-甲硅烷基取代的苯并噻吩，可用作合成2，3-不对称取代的苯并噻吩的通用平台。