Methyl 3-cyclopentyl-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-6-carboxylate | 905856-76-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Methyl 3-cyclopentyl-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-6-carboxylate
• CAS: 905856-76-0
• 化学式: C₂₂H₃₀BNO₄
• 分子量: 383.295
• InChiKey: IIXPGONVTYQVBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 3-cyclopentyl-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-6-carboxylate 在 potassium phosphate 、 三叔丁基膦 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 水 、 异丙醇 为溶剂， 反应 1.5h， 生成 3-环戊基-1-甲基-1H-吲哚-6-羧酸异丙酯
  参考文献：
  名称：

  A Highly Concise and Convergent Synthesis of HCV Polymerase Inhibitor Deleobuvir (BI 207127): Application of a One-Pot Borylation–Suzuki Coupling Reaction

  摘要：

  A highly concise and convergent synthesis of HCV polymerase inhibitor Deleobuvir (BI 207127, 1) was achieved, featuring efficient Pd-catalyzed one-pot borylation-Suzuki coupling where TFP was identified as the unique ligand effective for these transformations.

  DOI：

  10.1021/ol5021114
• 作为产物：
  描述：

  6-吲哚甲酸 在 palladium on activated charcoal 、 氢气 、 溴 、 palladium diacetate 、 potassium carbonate 、 三乙胺 、 potassium hydroxide 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 N-甲基吡咯烷酮 、 乙二醇二甲醚 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 Methyl 3-cyclopentyl-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-6-carboxylate
  参考文献：
  名称：

  A Highly Concise and Convergent Synthesis of HCV Polymerase Inhibitor Deleobuvir (BI 207127): Application of a One-Pot Borylation–Suzuki Coupling Reaction

  摘要：

  A highly concise and convergent synthesis of HCV polymerase inhibitor Deleobuvir (BI 207127, 1) was achieved, featuring efficient Pd-catalyzed one-pot borylation-Suzuki coupling where TFP was identified as the unique ligand effective for these transformations.

  DOI：

  10.1021/ol5021114

文献信息

• Process for preparing 2, 3-disubstituted indoles
  申请人：Khodabocus Ahmad

  公开号：US20060183752A1

  公开（公告）日：2006-08-17

  Disclosed are processes for making 2,3 disubstituted indole compounds such as compounds of general formula I comprised of the steps of a) reacting a bromoindole compound (i) with a dialkoxyl C 1-5 borane in the presence of a ligand, a palladium catalyst and a base to make a compound of general formula (ii); or alternatively reacting compound (i) with a trialkyl magnesiate reagent, followed by treatment with a borate; b) reacting the product of step a with a R2-Hal where R2-Hal is defined herein.

  披露了制备2,3-二取代吲哚化合物的方法，例如通式I所示的化合物，包括以下步骤： a) 在存在配体、钯催化剂和碱的情况下，将溴吲哚化合物(i)与二烷氧基C1-5硼烷反应，制备通式(ii)化合物；或者将化合物(i)与三烷基镁试剂反应，然后用硼酸盐处理；b) 将步骤a的产物与R2-Hal反应，其中R2-Hal在此处定义。
• Conformation-Based Restrictions and Scaffold Replacements in the Design of Hepatitis C Virus Polymerase Inhibitors: Discovery of Deleobuvir (BI 207127)
  作者：Steven R. LaPlante、Michael Bös、Christian Brochu、Catherine Chabot、René Coulombe、James R. Gillard、Araz Jakalian、Martin Poirier、Jean Rancourt、Timothy Stammers、Bounkham Thavonekham、Pierre L. Beaulieu、George Kukolj、Youla S. Tsantrizos

  DOI：10.1021/jm4011862

  日期：2014.3.13

  Conformational restrictions of flexible torsion angles were used to guide the identification of new chemotypes of HCV NS5B inhibitors. Sites for rigidification were based on an acquired conformational understanding of compound binding requirements and the roles of substituents in the free and bound states. Chemical bioisosteres of amide bonds were explored to improve cell-based potency. Examples are shown, including the design concept that led to the discovery of the phase III clinical candidate deleobuvir (BI 207127). The structure-based strategies employed have general utility in drug design.
• A Highly Concise and Convergent Synthesis of HCV Polymerase Inhibitor Deleobuvir (BI 207127): Application of a One-Pot Borylation–Suzuki Coupling Reaction
  作者：Yongda Zhang、Bruce Z. Lu、Guisheng Li、Sonia Rodriguez、Jonathan Tan、Han-Xun Wei、Jianxiu Liu、Frank Roschangar、Fei Ding、Wenyi Zhao、Bo Qu、Diana Reeves、Nelu Grinberg、Heewon Lee、Golo Heckmann、Oliver Niemeier、Michael Brenner、Youla Tsantrizos、Pierre L. Beaulieu、Azad Hossain、Nathan Yee、Vittorio Farina、Chris H. Senanayake

  DOI：10.1021/ol5021114

  日期：2014.9.5

  A highly concise and convergent synthesis of HCV polymerase inhibitor Deleobuvir (BI 207127, 1) was achieved, featuring efficient Pd-catalyzed one-pot borylation-Suzuki coupling where TFP was identified as the unique ligand effective for these transformations.