1-{4-[(3-bromo-5-methylpyridin-2-yl)amino]phenyl}ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-{4-[(3-bromo-5-methylpyridin-2-yl)amino]phenyl}ethanone
• 英文别名: 1-[4-[(3-bromo-5-methylpyridin-2-yl)amino]phenyl]ethanone
• 化学式: C₁₄H₁₃BrN₂O
• 分子量: 305.174
• InChiKey: FKVXFECCEJNUHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-{4-[(3-bromo-5-methylpyridin-2-yl)amino]phenyl}ethanone 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 3.0h， 以14.7%的产率得到1-(3-methyl-9H-pyrido[2,3-b]indol-6-yl)ethanone
  参考文献：
  名称：

  WO2008/16184

  摘要：

  公开号：
• 作为产物：
  描述：

  4-碘代苯乙酮 、 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 6.17h， 以45%的产率得到1-{4-[(3-bromo-5-methylpyridin-2-yl)amino]phenyl}ethanone
  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：——
• 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.