3-bromo-5-methyl-N-1-naphthylpyridine-2-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-bromo-5-methyl-N-1-naphthylpyridine-2-amine
• 英文别名: 3-bromo-5-methyl-N-naphthalen-1-ylpyridin-2-amine
• 化学式: C₁₆H₁₃BrN₂
• 分子量: 313.197
• InChiKey: BCKFMYVLGFSQCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-5-methyl-N-1-naphthylpyridine-2-amine 在 Catalyst obtained from palladium(II) acetate and 2-(dicyclohexylphosphino)biphenyl 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 3.5h， 以86.8%的产率得到8-methyl-11H-benzo[g]pyrido[2,3-b]indole
  参考文献：
  名称：

  WO2008/16184

  摘要：

  公开号：
• 作为产物：
  描述：

  1-碘萘 、 2-氨基-3-溴-5-甲基吡啶 在 Catalyst obtained from palladium(II) acetate and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene caesium carbonate 作用下， 以 苯甲醚 为溶剂， 反应 8.25h， 以63%的产率得到3-bromo-5-methyl-N-1-naphthylpyridine-2-amine
  参考文献：
  名称：

  WO2008/16184

  摘要：

  公开号：

文献信息

• ALPHA-CARBOLINE DERIVATIVES AND METHODS FOR PREPARATION THEREOF
  申请人：Mizuno Masahiro

  公开号：US20090326229A1

  公开（公告）日：2009-12-31

  To provide methods for preparing alpha-carboline derivatives in few steps, as well as conveniently and industrially advantageously. A method for preparation of a compound represented by Formula (II) or a salt thereof, comprising subjecting a compound represented by Formula (I) or a salt thereof to a ring closure reaction in the presence of a palladium catalyst, a ligand, and a base; a method for preparation of a compound represented by Formula (IX) or a salt thereof, comprising subjecting a compound represented by Formula (VII) or a salt thereof to a ring closure reaction in the presence of a palladium catalyst, a ligand, and a base, and subsequently to an aromatization reaction; and methods for preparation of compounds represented by Formulae (XV), (XVII), and (XIX) or a salt thereof, comprising subjecting respective compounds represented by Formulae (II) and (IX) or a salt thereof to a reaction for introducing a leaving group when necessary, and subsequently to a coupling reaction: wherein the symbols respectively represent the same meaning as defined in the present specification.

  提供几步制备α-咔啉衍生物的方法，以及方便和具有工业优势的方法。一种制备式（II）化合物或其盐的方法，包括在钯催化剂、配体和碱的存在下，将式（I）化合物或其盐进行环闭合反应；一种制备式（IX）化合物或其盐的方法，包括在钯催化剂、配体和碱的存在下，将式（VII）化合物或其盐进行环闭合反应，然后进行芳构化反应；以及制备式（XV）、（XVII）和（XIX）化合物或其盐的方法，包括在必要时将式（II）和（IX）化合物或其盐分别进行引入离去基团的反应，然后进行偶联反应：其中符号分别表示本说明书中定义的相同含义。
• WO2008/16184
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] ALPHA-CARBOLINE DERIVATIVES AND METHODS FOR PREPARATION THEREOF<br/>[FR] DÉRIVÉS DE L'ALPHA CARBOLINE ET LEURS PROCÉDÉS DE PRÉPARATION
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2008016184A1

  公开（公告）日：2008-02-07

  [EN] To provide methods for preparing alpha-carboline derivatives in few steps, as well as conveniently and industrially advantageously. A method for preparation of a compound represented by Formula (II) or a salt thereof, comprising subjecting a compound represented by Formula (I) or a salt thereof to a ring closure reaction in the presence of a palladium catalyst, a ligand, and a base; a method for preparation of a compound represented by Formula (IX) or a salt thereof, comprising subjecting a compound represented by Formula (VII) or a salt thereof to a ring closure reaction in the presence of a palladium catalyst, a ligand, and a base, and subsequently to an aromatization reaction; and methods for preparation of compounds represented by Formulae (XV), (XVII), and (XIX) or a salt thereof, comprising subjecting respective compounds represented by Formulae (II) and (IX) or a salt thereof to a reaction for introducing a leaving group when necessary, and subsequently to a coupling reaction: wherein the symbols respectively represent the same meaning as defined in the present specification.
  [FR] L'invention concerne des procédés, destinés à préparer des dérivés de l'alpha carboline en un nombre d'étapes limité, et qui permettent également une production industrielle sûre et pratique. L'invention concerne un procédé de préparation d'un composé représenté par la formule (II), ou un sel de celui-ci, consistant à soumettre un composé représenté par la formule (I), ou un sel de celui-ci, à une réaction de cyclisation en présence d'un catalyseur à base de palladium, d'un ligand et d'une base ; un procédé de préparation d'un composé représenté par la formule (IX), ou un sel de celui-ci, consistant à soumettre un composé représenté par la formule (VII), ou un sel de celui-ci, à une réaction de cyclisation en présence d'un catalyseur à base de palladium, d'un ligand et d'une base, puis à une réaction d'aromatisation ; et des procédés de préparation de composés représentés par les formules (XV), (XVII) et (XIX), ou un sel de ceux-ci, consistant à soumettre les composés correspondants représentés par les formules (II) et (IX), ou un sel de ceux-ci, à une réaction destinée à introduire un groupe partant lorsque nécessaire, puis à une réaction de couplage, les symboles ayant respectivement la même signification que celle définie dans la description.
• Rapid access to diverse α-carbolines through sequential transition metal catalyzed amination and direct C–H arylation
  作者：Masahiro Mineno、Misayo Sera、Tsuyoshi Ueda、Masahiro Mizuno、Mitsuhisa Yamano、Hideya Mizufune、Atsuhiko Zanka

  DOI：10.1016/j.tet.2014.06.100

  日期：2014.9

  An efficient sequence of Pd catalyzed amination and direct C-H arylation for a synthesis of pharmacologically important alpha-carbolines is described. The outstanding feature in the synthetic sequence is that a combination of DBU and 2-(dicyclohexylphosphino)biphenyl (DCHPB) plays a critical role to not only enhance the reactivity but also suppress hydrodehalogenation in the direct C-H arylation step. The reaction protocol provides alpha-carbolines with various substituents including base-sensitive ester and ketone moieties in moderate to excellent yields. Moreover, combination with Cu catalyzed amination further enhanced the versatility of the alpha-carboline synthesis. (C) 2014 Elsevier Ltd. All rights reserved.