Production Method 1

898289-06-0

Reaction Conditions

1.1 Reagents: 1,1,3,3-Tetramethyldisiloxane ,  Tripotassium phosphate Catalysts: Dichlorobis(tricyclohexylphosphine)nickel Solvents: Toluene ;  15 h, 120 °C

Reference

Cine substitution of arenes using the aryl carbamate as a removable directing group

Mesganaw, Tehetena; Fine Nathel, Noah F.; Garg, Neil K., Organic Letters, 2012, 14(11), 2918-2921

Production Method 2

25015-63-8

590417-55-3

898289-06-0

Reaction Conditions

1.1 Catalysts: Palladium diacetate ,  2-(Dicyclohexylphosphino)biphenyl Solvents: 1,4-Dioxane ;  rt; 30 min, rt
1.2 Reagents: Triethylamine Solvents: 1,4-Dioxane ;  rt; 2 - 8 h, 80 °C

Reference

Convenient synthesis of 1H-indol-1-yl boronates via palladium(0)-catalyzed borylation of bromo-1H-indoles with 'pinacolborane'

Stadlwieser, Josef F.; Dambaur, Markus E., Helvetica Chimica Acta, 2006, 89(5), 936-946

Production Method 3

73183-34-3

590417-55-3

898289-06-0

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  16 h, 80 °C

Reference

Heterocyclic Chromophore Amphiphiles and their Supramolecular Polymerization

Djordjevic, Luka; Sai, Hiroaki ; Yang, Yang ; Sather, Nicholas A. ; Palmer, Liam C. ; et al, Angewandte Chemie, 2023, 62(17),

Production Method 4

388116-27-6

898289-06-0

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  0 °C; 15 min, 0 °C → rt
1.2 Solvents: Dimethylformamide ;  0 °C; 0 °C → rt; 1 h, rt
1.3 Reagents: Ammonium chloride Solvents: Water ;  0 °C

Reference

Catalytic (3 + 2) annulation of donor-acceptor aminocyclopropane monoesters and indoles

Pirenne, Vincent; Robert, Emma G. L.; Waser, Jerome, Chemical Science, 2021, 12(25), 8706-8712

Production Method 5

73183-34-3

898289-06-0

Reaction Conditions

1.1 Catalysts: Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]dirhodium ,  1,3-Dihydro-4,5-dimethyl-1,3-bis(2,4,6-trimethylphenyl)-2H-imidazol-2-ylidene Solvents: Toluene ;  5 min, rt
1.2 Solvents: Toluene ;  rt; 15 h, 130 °C

Reference

Rhodium-catalyzed borylation of aryl 2-pyridyl ethers through cleavage of the carbon-oxygen bond: borylative removal of the directing group

Kinuta, Hirotaka; Tobisu, Mamoru; Chatani, Naoto, Journal of the American Chemical Society, 2015, 137(4), 1593-1600

Production Method 6

73183-34-3

7556-37-8

898289-06-0

Reaction Conditions

1.1 Reagents: Tripotassium phosphate ,  Methanaminium, N-[(dimethylamino)fluoromethylene]-N-methyl-, hexafluorophosphate… Catalysts: Bis(1,5-cyclooctadiene)nickel ,  Tricyclohexylphosphine Solvents: 1,4-Dioxane ;  24 h, 60 °C

Reference

Ni-Catalyzed Deoxygenative Borylation of Phenols Via O-Phenyl-uronium Activation

Liu, Xiaojie; Xu, Biping; Su, Weiping, ACS Catalysis, 2022, 12(15), 8904-8910

Production Method 7

388116-27-6

898289-06-0

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  0 °C; 15 min, 0 °C; 1 h, rt; rt → 0 °C
1.2 0 °C → rt; 30 min, rt; rt → 0 °C
1.3 Reagents: Ammonium chloride Solvents: Water ;  0 °C

Reference

Iron-iodine co-catalysis towards tandem C-N/C-C bond formation: one-pot regioselective synthesis of 2-amino-3-alkylindoles

Zhang, Yingying; Huang, Yating; Yu, Kewei; Zhang, Xiaoxiang; Yu, Wenhua; et al, Organic Chemistry Frontiers, 2022, 9(22), 6165-6171

Production Method 8

388116-27-6

898289-06-0

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  0 °C; 15 min, 0 °C; 1 h, rt; rt → 0 °C
1.2 0 °C → rt; 30 min, rt; rt → 0 °C
1.3 Reagents: Ammonium chloride Solvents: Water

Reference

Copper-iodine co-catalyzed C-H aminoalkenylation of indoles via temperature-controlled selectivity switch: facile synthesis of 2-azolyl-3-alkenylindoles

Zhang, Xiaoxiang; Yu, Wenhua; Nie, Yiyu; Zhang, Yingying; Gu, Xiaoting; et al, Organic Chemistry Frontiers, 2022, 9(14), 3794-3799

1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Raw materials

• 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• Bis(pinacolato)diborane
• Pinacolborane
• 4-Bromo-1-methyl-1H-indole
• 1-Methyl-1H-indol-4-OL

1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Preparation Products

• 1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (898289-06-0)

• 1. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
• 2. Emergence of microfluidic wearable technologies
  Joo Chuan Yeo,Kenry Lab Chip, 2016,16, 4082-4090
• 3. Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation
  Matthew J. Gaunt,Jinquan Yu,Jonathan B. Spencer Chem. Commun., 2001, 1844-1845
• 4. Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)?
  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 5. Evolution of cellulose into flexible conductive green electronics: a smart strategy to fabricate sustainable electrodes for supercapacitors
  Tengfei Yu,Yuehan Wu,Wei Li,Bin Li RSC Adv., 2014,4, 34134-34143

Introduction to 1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (CAS No. 898289-06-0) and Its Emerging Applications in Chemical Biology

The compound 1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, identified by the CAS number 898289-06-0, represents a significant advancement in the realm of organic synthesis and pharmaceutical development. This molecule, characterized by its intricate boronic ester functionality and indole core, has garnered considerable attention due to its versatile applications in medicinal chemistry and biotechnology. The structural motif of this compound combines the stability of a tetramethylborate group with the bioactivity of an indole scaffold, making it a valuable intermediate in the synthesis of novel therapeutic agents.

In recent years, boronic acid derivatives have emerged as pivotal tools in drug discovery, owing to their ability to participate in selective cross-coupling reactions such as Suzuki-Miyaura couplings. The presence of the tetramethyl-1,3,2-dioxaborolan-2-yl moiety in 1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole enhances its reactivity while minimizing unwanted side reactions, thereby facilitating efficient synthetic pathways. This feature has been exploited in the development of small-molecule inhibitors targeting various biological pathways, including those implicated in cancer and neurodegenerative diseases.

One of the most compelling aspects of this compound is its potential application in the synthesis of indole-based drugs. Indole derivatives are well-documented for their broad spectrum of biological activities, ranging from antimicrobial to anti-inflammatory effects. The introduction of a boronic ester group at the 4-position of the indole ring allows for further functionalization via cross-coupling reactions, enabling the construction of structurally diverse analogs. Such modifications are crucial for optimizing pharmacokinetic properties and enhancing target specificity.

Recent studies have highlighted the role of 1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole in the development of novel anticancer agents. Researchers have leveraged its reactivity to generate bisindole scaffolds, which have shown promising activity against multiple drug-resistant cancer cell lines. The boronic ester functionality serves as a handle for introducing additional pharmacophores through palladium-catalyzed coupling reactions, leading to compounds with enhanced cytotoxicity and reduced toxicity profiles. These findings underscore the compound's significance as a building block in oncology research.

The compound's utility extends beyond oncology; it has also been explored in the context of central nervous system (CNS) disorders. Indole derivatives are known to interact with various neurotransmitter systems, making them attractive candidates for treating conditions such as Alzheimer's disease and Parkinson's disease. By incorporating a boronic ester group into the indole core, chemists can fine-tune molecular properties to improve blood-brain barrier penetration and target neuronal receptors more effectively. Preliminary data suggest that derivatives of 1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole exhibit neuroprotective effects in cellular models.

The synthetic accessibility of this compound is another key factor contributing to its widespread adoption in research laboratories. Modern synthetic methodologies have enabled efficient preparation of 1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, making it readily available for further derivatization. This accessibility is particularly important for high-throughput screening campaigns aimed at identifying lead compounds for drug development. Additionally, the stability of the boronic ester group under various reaction conditions ensures that synthetic transformations can be conducted with high yields and minimal decomposition.

In conclusion,1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (CAS No. 898289-06-0) represents a cornerstone in modern medicinal chemistry due to its unique structural features and broad applicability. Its role as a key intermediate in cross-coupling reactions has opened up new avenues for drug discovery across multiple therapeutic areas. As research continues to uncover novel biological activities and synthetic strategies involving this compound,its significance is expected to grow further, solidifying its position as an indispensable tool in pharmaceutical innovation.

• 642494-36-8(6-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole)
• 1021868-08-5(5-(Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline)
• 884507-19-1(1-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole)
• 388116-27-6(4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole)
• 1035458-54-8(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline)
• 837392-62-8(1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole)
• 917773-22-9(9H-Carbazole,9-dodecyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-)
• 269410-24-4(Indole-5-boronic acid, pinacol ester)
• 903499-35-4(1-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole)
• 683229-61-0(1-methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole)