2-(5-bromoindolin-1-yl)-1H-benzo[d]imidazole | 1357142-87-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(5-bromoindolin-1-yl)-1H-benzo[d]imidazole
• 英文别名: 2-(5-bromo-2,3-dihydro-1H-indol-1-yl)-1H-benzimidazole；2-(5-bromo-2,3-dihydroindol-1-yl)-1H-benzimidazole
• CAS: 1357142-87-0
• 化学式: C₁₅H₁₂BrN₃
• 分子量: 314.184
• InChiKey: FQQXDWSOPCQSEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  31.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-bromoindolin-1-yl)-1H-benzo[d]imidazole 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四(三苯基膦)钯 potassium acetate 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 水 为溶剂， 反应 13.0h， 生成 3-[1-(1H-benzimidazol-2-yl)-2,3-dihydro-1H-indol-5-yl]-1-ethyl-1H-pyrazolo[4,3-b]pyridine
  参考文献：
  名称：

  [EN] FUSED HETEROCYCLIC COMPOUNDS
  [FR] COMPOSÉS HÉTÉROCYCLIQUES CONDENSÉS

  摘要：

  本发明提供了一种具有PDE 10A抑制作用的化合物，可用作预防或治疗精神分裂症等疾病的药物。化合物的结构如下（1'）：其中，环A'代表可选择取代的吡啶环、可选择取代的吡啉环、嘧啶环或吡嗪环，R1'代表（1）其中，R1a'代表可选择取代的苯基或可选择取代的5-至10-成员杂环基，环B2代表键、-S-、-O-、-CO-、可选择取代的亚甲基基团或-NRa'-（Ra'代表氢原子或可选择取代的C1-6烷基基团），环B1'代表可选择进一步取代的6-至10-成员芳香碳氢环、或可选择进一步取代的5-至10-成员芳香杂环环，或者，L'和R1a'可以结合形成可选择取代的双环或三环融合杂环基，或（2）其中，R1b'代表可选择取代的苯基或可选择取代的5-至10-成员杂环基，环B2'代表可选择取代的苯环、可选择取代的吡啶环、可选择取代的嘧啶环、可选择取代的吡嗪环或可选择取代的吡啉环，环D'代表可选择进一步取代的5-或6-成员环，R2'代表氢原子或取代基，X'代表=N-或=CRb'-（Rb'代表氢原子或取代基），_ _ _ _ _代表Rb'和R2'可能形成，与它们各自相邻的碳原子和氮原子一起，当X'为=CRb'-时，形成可选择取代的5-至7-成员环，或其盐。

  公开号：

  WO2012018909A1
• 作为产物：
  描述：

  5-溴二氢吲哚 在 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-(5-bromoindolin-1-yl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Rh(III)-Catalyzed [5 + 2] Oxidative Annulation of Cyclic Arylguanidines and Alkynes to 1,3-Benzodiazepines. A Striking Mechanistic Proposal from DFT

  摘要：

  A novel and mild Rh(III)-catalyzed [5 + 2] oxidative annulation between cyclic arylguanidines and alkynes efficiently affords 1,3-benzodiazepines (pentacyclic guanidines). The use of O-2 as the sole oxidant in place of commonly used metal oxidants such as AgOAc clearly improves the efficiency of the oxidative annulation process. The mechanism of the cycloaddition most likely involves the formation of an eight-membered rhodacycle. DFT calculations support a striking mechanistic proposal for the [5 + 2] oxidative annulation.

  DOI：

  10.1021/acs.orglett.9b00354

文献信息

• Ru(<scp>ii</scp>)-Catalyzed and acidity-controlled tunable [5+1]/[5+2] annulation for building ring-fused quinazolines and 1,3-benzodiazepines
  作者：Yurong Yang、Kaixin Zhang、Jian Yang、Guoxun Zhu、Weijie Chen、Chao Zhang、Zhi Zhou、Wei Yi

  DOI：10.1039/d0cc04041j

  日期：——

  Ru(ii)-Catalyzed and acidity-controlled tunable [5+1]/[5+2] annulation for the divergent synthesis of ring-fused quinazolines and 1,3-benzodiazepines has been developed.

  使用Ru(ii)催化和酸度控制的可调[5+1]/[5+2]环化反应，实现了环融合喹唑啉和1,3-苯并二氮杂环的分散合成。
• FUSED HETEROCYCLIC COMPOUNDS
  申请人：Raker Joseph

  公开号：US20130172292A1

  公开（公告）日：2013-07-04

  The present invention provides a compound which has the effect of PDE 10A inhibition, and which is useful as a medicament for preventing or treating schizophrenia or so on. A compound represented by the formula (1′): wherein, Ring A′ represents an optionally substituted pyridine ring, an optionally substituted pyridazine ring, a pyrimidine ring, or 10 a pyrazine ring, R1′ represents (1) wherein, R 1a′ represents an optionally substituted phenyl group, or an optionally substituted 5- to 10-membered heterocyclic group, Ring B2 represents a bond, —S—, -0-, —CO—, an optionally substituted methylene group, or —NR a′ -(R a′ represents a hydrogen atom, or an optionally substituted C 1-6 alkyl group), and Ring B 1′ represents an optionally further substituted 6- to 10-membered aromatic hydrocarbon ring, or an optionally further substituted 5- to 10-membered aromatic heterocyclic ring, or alternatively, L′ and R 1a′ may be taken together to form an optionally substituted bicyclic or tricyclic fused heterocyclic group, or (2), wherein, R 1b′ represents an optionally substituted phenyl group, or an optionally substituted 5- to 10-membered heterocyclic group, Ring B 2′ represents an optionally substituted benzene ring, an optionally substituted pyridine ring, an optionally substituted pyrimidine ring, an optionally substituted pyrazine ring, or an optionally substituted pyridazine ring, Ring D′ represents an optionally further substituted 5- or 6-membered ring, R 2′ represents a hydrogen atom, or a substituent, X′ represents ═N— or ═CR b′ —(R b′ represents a hydrogen atom, or a substituent), - - - - - represents that R b′ and R 2′ may form, taken together with the carbon atom and the nitrogen atom to which they are each adjacent, an optionally substituted 5- to 7-membered ring when.X′ is ═CR b′ , or a salt thereof.

  本发明提供一种具有PDE 10A抑制作用的化合物，可用作预防或治疗精神分裂症等药物。化合物表示为公式（1'）：其中，环A'表示可选取取代的吡啶环、可选取取代的吡嗪环、嘧啶环或吡嗪环，R1'表示（1）其中，R1a'表示可选取取代的苯基或可选取取代的5-至10-成员杂环基，环B2表示键、-S-、-O-、可选取取代的亚甲基基或-NRa'（Ra'表示氢原子或可选取取代的C1-6烷基基），环B1'表示可选进一步取代的6-至10-成员芳香烃环或可选进一步取代的5-至10-成员芳香杂环环，或者，L'和R1a'可取代成为可选取代的双环或三环融合杂环基，或（2），其中，R1b'表示可选取取代的苯基或可选取取代的5-至10-成员杂环基，环B2'表示可选取取代的苯环、可选取取代的吡啶环、可选取取代的嘧啶环、可选取取代的吡嗪环或可选取取代的吡嗪环，环D'表示可选进一步取代的5-或6-成员环，R2'表示氢原子或取代基，X'表示═N-或═CRb'-（Rb'表示氢原子或取代基），- - - - - 表示当X'为═CRb'时，Rb'和R2'可与它们各自相邻的碳原子和氮原子一起形成可选取代的5-至7-成员环，或其盐。
• Fused heterocyclic compounds
  申请人：Raker Joseph

  公开号：US09029536B2

  公开（公告）日：2015-05-12

  The present invention provides a compound which has the effect of PDE 10A inhibition, and which is useful as a medicament for preventing or treating schizophrenia or so on. A compound represented by the formula (1′): wherein, Ring A′ represents an optionally substituted pyridine ring, an optionally substituted pyridazine ring, a pyrimidine ring, or 10 a pyrazine ring, R1′ represents (1) wherein, R1a′ represents an optionally substituted phenyl group, or an optionally substituted 5- to 10-membered heterocyclic group, Ring B2 represents a bond, —S—, -0-, —CO—, an optionally substituted methylene group, or —NRa′— (Ra′ represents a hydrogen atom, or an optionally substituted C1-6 alkyl group), and Ring B1′ represents an optionally further substituted 6- to 10-membered aromatic hydrocarbon ring, or an optionally further substituted 5- to 10-membered aromatic heterocyclic ring, or alternatively, L′ and R1a′ may be taken together to form an optionally substituted bicyclic or tricyclic fused heterocyclic group, or (2), wherein, R1b′ represents an optionally substituted phenyl group, or an optionally substituted 5- to 10-membered heterocyclic group, Ring B2′ represents an optionally substituted benzene ring, an optionally substituted pyridine ring, an optionally substituted pyrimidine ring, an optionally substituted pyrazine ring, or an optionally substituted pyridazine ring, Ring D′ represents an optionally further substituted 5- or 6-membered ring, R2′ represents a hydrogen atom, or a substituent, X′ represents ═N— or ═CRb′—(Rb′ represents a hydrogen atom, or a substituent), - - - - - represents that Rb′ and R2′ may form, taken together with the carbon atom and the nitrogen atom to which they are each adjacent, an optionally substituted 5- to 7-membered ring when.X′ is ═CRb′, or a salt thereof.

  本发明提供了一种具有PDE 10A抑制作用的化合物，可用作预防或治疗精神分裂症等药物。化合物的结构式为（1'）：其中，环A'表示可选取取代的吡啶环、可选取取代的吡嗪环、嘧啶环或吡嗪环，R1'表示（1），其中R1a'表示可选取取代的苯基或可选取取代的5-至10-成员杂环基，环B2表示键、-S-、-O-、可选取取代的亚甲基基或-NRa'-(Ra'表示氢原子或可选取取代的C1-6烷基基)，环B1'表示可选取进一步取代的6-至10-成员芳香碳环或可选取进一步取代的5-至10-成员芳香杂环，或者，L'和R1a'可取代成为可选取代的双环或三环融合杂环基，或（2），其中R1b'表示可选取取代的苯基或可选取取代的5-至10-成员杂环基，环B2'表示可选取取代的苯环、可选取取代的吡啶环、可选取取代的嘧啶环、可选取取代的吡嗪环或可选取取代的吡嗪嗪环，环D'表示可选进一步取代的5-或6-成员环，R2'表示氢原子或取代基，X'表示═N-或═CRb'-（Rb'表示氢原子或取代基），- - - - - 表示当X'为═CRb'时，Rb'和R2'可以与它们各自相邻的碳原子和氮原子一起形成可选取代的5-至7-成员环，或其盐。
• Assembly of fluorinated benzodiazepines <i>via</i> Rh(<scp>iii</scp>)-catalysed [5+2] annulation of <i>N</i>-benzo[<i>d</i>]imidazole indolines with 2,2-difluorovinyl tosylate
  作者：Fu-Xiaomin Liu、Weijie Chen、Lei Ma、Kui Cheng、Zhi Zhou、Wei Yi

  DOI：10.1039/d3nj01544k

  日期：——

  an unusual 1,2-regioselectivity for the chemodivergent construction of monofluorinated and gem-difluorinated benzodiazepines, which are defined as potent anti-tumor agents against different cancer cell lines. In general, this work provides a powerful complement to both C–H activation chemistry and anti-tumor lead discovery.

  在此，我们实现了一种高效且溶剂可调的Rh( III )催化的N-苯并[ d ]咪唑二氢吲哚与2,2-二氟乙烯基甲苯磺酸酯的[5+2]成环反应，该反应呈现出不寻常的1,2-区域选择性。单氟化和双氟化苯二氮卓类药物的化学发散结构，被定义为针对不同癌细胞系的有效抗肿瘤剂。总的来说，这项工作为 C-H 活化化学和抗肿瘤先导化合物的发现提供了强有力的补充。
• Rhodium(III)‐Catalyzed C7‐Spiroannulation of Indolines with Maleimides: Facile Access to Aza‐Spiromulticycles
  作者：Jinfang Zhao、Chao Pi、Yangjie Wu、Xiuling Cui

  DOI：10.1002/adsc.202301463

  日期：2024.4.23

  Herein, we report a chemo‐ and regioselective Rh‐catalyzed redox C7‐spiroannulation reaction of N‐benzo[d]imidazole indolines with maleimides, resulting in a series of N‐benzo[d]imidazole indoline fused azaspirocycles in up to 92% yield. The synthetic utility is demonstrated by the synthesis of highly functionalized nitrogen‐containing spiropolycyclic skeletons. The annulation reaction could also be performed with maleic esters and acrylates. The products were purified by simple filtration. The Rh catalyst can be recycled, and the reaction could be performed at gram‐scale using 0.5 mol% of catalyst, which makes this protocol potentially applicable in industry. Moreover, the efficient post‐modification of pharmaceutical molecules demonstrates its practicability.

  摘要我们在此报告了一种由 Rh 催化的 N-苯并[d]咪唑吲哚啉与马来酰亚胺的化学和区域选择性 C7-螺烷化反应，从而得到一系列 N-苯并[d]咪唑吲哚啉融合的氮杂环，收率高达 92%。通过合成高度官能化的含氮双环骨架，证明了该合成方法的实用性。环化反应也可与马来酸酯和丙烯酸酯一起进行。产物可通过简单过滤进行纯化。Rh 催化剂可以循环使用，只需使用 0.5 摩尔%的催化剂就可以在克级规模上进行反应，这使得该方案有望应用于工业领域。此外，药物分子的高效后改性也证明了它的实用性。