N-(5-溴吡啶-2-基)-2,2-二甲基丙酰胺 | 182344-63-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(5-溴吡啶-2-基)-2,2-二甲基丙酰胺
• 中文别名: N-(5-溴-吡啶-2-)-2,2-二甲基丙酰胺
• 英文名称: N-(5-bromopyridin-2-yl)pivalamide
• 英文别名: N-(5-bromo-pyridin-2-yl)-2,2-dimethyl-propionamide；N-(5-bromopyridin-2-yl)-2,2-dimethylpropanamide
• CAS: 182344-63-4
• 化学式: C₁₀H₁₃BrN₂O
• mdl: MFCD08110803
• 分子量: 257.13
• InChiKey: LHJMFFKVXROWOC-UHFFFAOYSA-N

物化性质

• 沸点：
  380.1±27.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(5-溴吡啶-2-基)-2,2-二甲基丙酰胺 在 盐酸 、 silver hexafluoroantimonate 、 [Cp*RhCl2]2 、 copper diacetate 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 27.0h， 生成 Methyl 3-(2-amino-5-bromopyridin-3-yl)prop-2-enoate
  参考文献：
  名称：

  Rhodium(III)-Catalyzed Oxidative Olefination of Pyridines and Quinolines: Multigram-Scale Synthesis of Naphthyridinones

  摘要：

  A Rh(III)-catalyzed oxidative olefination of pyridines and quinolines has been achieved. This method has a broad substrate scope and has been applied to the expeditious, multigram-scale synthesis of naphthyridinones.

  DOI：

  10.1021/ol401540k
• 作为产物：
  描述：

  在 四羟基二硼 作用下， 反应 0.17h， 以76 mg的产率得到N-(5-溴吡啶-2-基)-2,2-二甲基丙酰胺
  参考文献：
  名称：

  Rapid and Selective in situ Reduction of Pyridine-N-oxides with Tetra­hydroxydiboron

  摘要：

  Pyridine-N-oxides are often used as reactive precursors in the syntheses of substituted pyridines. Isolation and subsequent reduction of the associated pyridine-N-oxide intermediates can be challenging. We have discovered that tetrahydroxydiboron functions as a mild, versatile, and remarkably selective reducing agent for pyridine-N-oxides and may be used in an in situ fashion, thus obviating the isolation of N-oxide-containing intermediates

  DOI：

  10.1055/s-0033-1340010

文献信息

• Process for preparation of benzo[f]quinolinones
  申请人：Eli Lilly and Company

  公开号：US05578724A1

  公开（公告）日：1996-11-26

  A series of benzoquinolin-3-ones are pharmaceuticals effective in treating conditions consequent on both Type I and Type II 5.alpha.-reductase and their preparation is disclosed.

  一系列苯醌啉-3-酮类药物在治疗由I型和II型5α-还原酶引起的疾病方面具有有效性，并且其制备方法已被披露。
• ETHYNYL DERIVATIVES
  申请人：Hoffmann-La Roche Inc.

  公开号：US20130090347A1

  公开（公告）日：2013-04-11

  The present invention relates to ethynyl derivatives of formula I wherein U, V, W, Y, R, R 1 , R 2 , R 3 and R 3′ are as described herein. It has been found that the compounds of general formula I are allosteric modulators of the metabotropic glutamate receptor subtype 5 (mGluR5).

  本发明涉及公式I的乙炔衍生物，其中U、V、W、Y、R、R1、R2、R3和R3'如本文所述。已发现一般公式I的化合物是代谢型谷氨酸受体亚型5（mGluR5）的别构调节剂。
• Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides Using Near Stoichiometric Carbon Monoxide
  作者：Karoline T. Neumann、Simon R. Laursen、Anders T. Lindhardt、Benny Bang-Andersen、Troels Skrydstrup

  DOI：10.1021/ol5007289

  日期：2014.4.18

  A general procedure for the palladium-catalyzed carbonylative Sonogashira coupling of aryl bromides is reported, using near stoichiometric amounts of carbon monoxide. The method allows a broad substrate scope in moderate to excellent yields. The formed alkynone motive serves as a platform for synthesis of various heterocyclic structures, including pyrimidines. Furthermore, the presented strategy allows

  据报道，使用接近化学计量的一氧化碳，钯催化芳基溴化物的羰基化Sonogashira偶联反应的一般程序。该方法允许以中等至优异的产率在宽范围的基材上使用。形成的炔酮动机用作合成各种杂环结构（包括嘧啶）的平台。此外，提出的策略允许有效的13 C标记。
• A convenient palladium catalyzed synthesis of symmetric biaryls, biheterocycles and biaryl chiral diamides
  作者：Shyamaprosad Goswami、Avijit Kumar Adak、Reshmi Mukherjee、Subrata Jana、Swapan Dey、John F. Gallagher

  DOI：10.1016/j.tet.2005.02.019

  日期：2005.4

  A series of symmetrical diamido biaryls has been synthesized in good yield by direct homocoupling of iodoarylbenzamides by palladium-catalysis. No cross product has been isolated from the reaction mixture of two different iodoarylbenzamides under similar conditions. However, only in the case of 2-iodo-N-phenylbenzamide, the intramolecularly coupled product phenanthridone has been isolated as a minor

  已经通过钯催化使碘代芳基苯甲酰胺直接均相偶联，以高收率合成了一系列对称的二酰胺基联芳基。在相似条件下，没有从两种不同的碘代芳基苯甲酰胺的反应混合物中分离出交叉产物。但是，仅在2-碘-N的情况下-苯基苯甲酰胺，分子内偶联产物菲啶酮已作为次要产物与主要的分子间偶联产物一起被分离出来。通过这种偶联方法已经合成了联苯手性二酰胺。该偶联反应还与官能化杂环化合物的还原二聚作用一起很好地起作用。因此，已经有效地合成了6,6'-二戊酰氨基-3,3'-联吡啶和6,6'-二甲基-2,2'-联吡啶。在两种情况下，已经解决了X射线晶体结构，以建立对称和​​手性的二氨基联芳基及其超分子网络的结构。
• [EN] ETHYNYL DERIVATIVES AS METABOTROPIC GLUTAMATE RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS D'ÉTHYNYLE COMME MODULATEURS DU RÉCEPTEUR MÉTABOTROPIQUE AU GLUTAMATE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013050460A1

  公开（公告）日：2013-04-11

  The present invention relates to ethynyl derivatives of formula I wherein Y is N or CH; with the proviso that Y can only be CH, if at least on of U, V or W are N; U is N or C-R4; V and W are independently N or CH; with the proviso that only one of U, V or W can be simultaneously nitrogen; R4 is hydrogen, methyl or halogen; R1 is phenyl or heteroaryl, which are optionally substituted by halogen, lower alkyl or lower alkoxy; R is hydrogen or lower alkyl; R2 is hydrogen, lower alkyl, lower alkoxy, CF3 or S-lower alkyl; are independently from each other hydrogen, lower alkyl or lower alkoxy; or R3 and R3 form together a C3-5-cycloalkyl-, tetrahydrofuran- or an oxetane-ring; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture, or to its corresponding enantiomer and/or optical isomer and/or stereoisomer thereof. It has been found that the compounds of general formula I are allosteric modulators of the metabotropic glutamate receptor subtype 5 (mGluR5).

  本发明涉及公式I的乙炔基衍生物，其中Y是N或CH；条件是，如果至少U、V或W中的一个是N，则Y只能是CH；U是N或C-R4；V和W独立地为N或CH；条件是U、V或W中只能同时有一个是氮；R4是氢、甲基或卤素；R1是苯基或杂芳基，它们可被卤素、低级烷基或低级烷氧基取代；R是氢或低级烷基；R2是氢、低级烷基、低级烷氧基、CF3或S-低级烷基；它们独立地是氢、低级烷基或低级烷氧基；或者R3和R3共同形成一个C3-5-环烷基、四氢呋喃或环氧环烷环；或者是一种药用可接受的酸加成盐，是一种外消旋混合物，或者是其相应的对映体和/或光学异构体和/或立体异构体。研究发现，通用公式I的化合物是代谢型谷氨酸受体亚型5（mGluR5）的别构调节剂。