2-氨基-5-溴-1H-吲哚-3-羧酸乙酯 | 1242140-62-0

• 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
• 中文名称: 2-氨基-5-溴-1H-吲哚-3-羧酸乙酯
• 英文名称: ethyl 2-amino-5-bromo-1H-indole-3-carboxylate
• CAS: 1242140-62-0
• 化学式: C₁₁H₁₁BrN₂O₂
• 分子量: 283.125
• InChiKey: JEEONSIWPYAQME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  68.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基-5-溴-1H-吲哚-3-羧酸乙酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 palladium on activated charcoal 、 氢气 、 三乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 N-甲基吡咯烷酮 、 甲醇 、 乙二醇甲醚 、 水 为溶剂， 反应 64.0h， 生成 tert-butyl 6-(1-(tert-butoxycarbonyl)piperidin-4-yl)-4-(4-((3-(tert-butyl)-1,2,4-oxadiazole-5-carboxamido)methyl)-3-methylphenyl)-9H-pyrimido[4,5-b]indole-9-carboxylate
  参考文献：
  名称：

  [EN] DEGRADATION OF BRUTON'S TYROSINE KINASE (BTK) BY CONJUGATION OF BTK INHIBITORS WITH E3 LIGASE LIGAND AND METHODS OF USE
  [FR] DÉGRADATION DE LA TYROSINE KINASE DE BRUTON (BTK) PAR CONJUGAISON D'INHIBITEURS DE BTK AVEC UN LIGAND DE LIGASE E3 ET MÉTHODES D'UTILISATION

  摘要：

  Disclosed herein are novel bifunctional compounds formed by conjugating BTK inhibitor moieties with E3 ligase Ligand moieties, which function to recruit targeted proteins to E3 ubiquitin ligase for degradation, and methods of preparation and uses thereof.

  公开号：

  WO2023125907A1
• 作为产物：
  描述：

  2-(5-溴-2-硝基苯基)-2-氰基乙酸乙酯 在 溶剂黄146 、 锌 作用下， 以34.6 %的产率得到2-氨基-5-溴-1H-吲哚-3-羧酸乙酯
  参考文献：
  名称：

  [EN] DEGRADATION OF BRUTON'S TYROSINE KINASE (BTK) BY CONJUGATION OF BTK INHIBITORS WITH E3 LIGASE LIGAND AND METHODS OF USE
  [FR] DÉGRADATION DE LA TYROSINE KINASE DE BRUTON (BTK) PAR CONJUGAISON D'INHIBITEURS DE BTK AVEC UN LIGAND DE LIGASE E3 ET MÉTHODES D'UTILISATION

  摘要：

  Disclosed herein are novel bifunctional compounds formed by conjugating BTK inhibitor moieties with E3 ligase Ligand moieties, which function to recruit targeted proteins to E3 ubiquitin ligase for degradation, and methods of preparation and uses thereof.

  公开号：

  WO2023125907A1

文献信息

• Lewis-Acid-Catalyzed Decarboxylative Annulation of 2-Aminoindole-3-Carboxylate with Ynals Involving [3 + 2] Spirocycloaddition and 2,3-Aza Migration
  作者：Manda Rajesh、Ravi Kumar、Surendra Puri、Jagadeesh Babu Nanubolu、Maddi Sridhar Reddy

  DOI：10.1021/acs.orglett.9b04626

  日期：2020.2.7

  2-Aminoindole-3-carboxylates undergo a Lewis-acid-catalyzed decarboxylative annulation with ynals to afford dihydro-chromeno-fused delta-carbolines through a 2,3-aza migration, via a spirocyclic intermediate generated from an initial [3 + 2] spirocycloaddition. Bronsted acid interference changes the path from a [3 + 2] to a [4 + 2] addition. 2-Aminoindoles without an ester functional group at C3 underwent a different condensation, followed by hetero-Diels Alder reaction to generate chromeno-fused alpha-carbolines.
• A Simple Copper-Catalyzed Cascade Synthesis of 2-Amino-1H-indole-3-carboxylate Derivatives
  作者：Xiaobo Yang、Hua Fu、Renzhong Qiao、Yuyang Jiang、Yufen Zhao

  DOI：10.1002/adsc.200900887

  日期：——

  AbstractWe have developed a simple and efficient copper‐catalyzed method for the synthesis of 2‐amino‐1H‐indole‐3‐carboxylate derivatives via cascade reactions of substituted N‐(2‐halophenyl)‐2,2,2‐trifluoroacetamide with alkyl 2‐cyanoacetate or malononitrile under mild conditions, and the method is of wide practical application.
• [EN] DEGRADATION OF BRUTON'S TYROSINE KINASE (BTK) BY CONJUGATION OF BTK INHIBITORS WITH E3 LIGASE LIGAND AND METHODS OF USE<br/>[FR] DÉGRADATION DE LA TYROSINE KINASE DE BRUTON (BTK) PAR CONJUGAISON D'INHIBITEURS DE BTK AVEC UN LIGAND DE LIGASE E3 ET MÉTHODES D'UTILISATION
  申请人：[en]BEIGENE, LTD.

  公开号：WO2023125907A1

  公开（公告）日：2023-07-06

  Disclosed herein are novel bifunctional compounds formed by conjugating BTK inhibitor moieties with E3 ligase Ligand moieties, which function to recruit targeted proteins to E3 ubiquitin ligase for degradation, and methods of preparation and uses thereof.