Production Method 1

206548-14-3

898747-24-5

Reaction Conditions

1.1 Reagents: Acetic anhydride Solvents: Chloroform
1.2 Reagents: Isoamyl nitrite ,  Potassium acetate ;  reflux

Reference

The discovery of diazepinone-based 5-HT3 receptor partial agonists

Manning, David D.; Guo, Cheng; Zhang, Zhenjun; Ryan, Kristen N.; Naginskaya, Jennifer; et al, Bioorganic & Medicinal Chemistry Letters, 2014, 24(11), 2578-2581

Production Method 2

1549643-27-7

898747-24-5

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Methanol ,  Water ;  2 h, rt

Reference

Linear propargylic alcohol functionality attached to the indazole-7-carboxamide as a JAK1-specific linear probe group

Kim, Mi Kyoung; Shin, Heerim; Cho, Seo Young; Chong, Youhoon, Bioorganic & Medicinal Chemistry, 2014, 22(3), 1156-1162

Methyl 5-bromo-1H-indazole-7-carboxylate Raw materials

• 1H-Indazole-7-carboxylic acid, 1-acetyl-5-bromo-, methyl ester
• Methyl 2-amino-5-bromo-3-methylbenzoate

Methyl 5-bromo-1H-indazole-7-carboxylate Preparation Products

• Methyl 5-bromo-1H-indazole-7-carboxylate (898747-24-5)

• 1. Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells?
  Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re Alsberg J. Mater. Chem. A, 2015,3, 9851-9860
• 2. 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
• 3. Fc microparticles can modulate the physical extent and magnitude of complement activity?
  David White,Sean R. Stowell Biomater. Sci., 2017,5, 463-474
• 4. Evolution in surface coverage of CH3NH3PbI3?XClXvia heat assisted solvent vapour treatment and their effects on photovoltaic performance of devices
  Dhirendra K. Chaudhary,Pramendra Kumar,Lokendra Kumar RSC Adv., 2016,6, 94731-94738
• 5. Dissociative dynamics of O2 on Ag(110)?
  Ivor Lon?ari? Phys. Chem. Chem. Phys., 2015,17, 9436-9445

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Halobenzoic acids and derivatives

Methyl 5-bromo-1H-indazole-7-carboxylate (CAS No. 898747-24-5): A Versatile Intermediate in Modern Pharmaceutical Synthesis

Methyl 5-bromo-1H-indazole-7-carboxylate (CAS No. 898747-24-5) is a significant intermediate in the realm of pharmaceutical synthesis, playing a pivotal role in the development of novel therapeutic agents. This compound, characterized by its brominated indazole core, has garnered considerable attention due to its structural versatility and functional reactivity, making it a valuable building block for medicinal chemists.

The Methyl 5-bromo-1H-indazole-7-carboxylate molecule exhibits a unique combination of electronic and steric properties that facilitate diverse chemical transformations. The presence of a bromine atom at the 5-position enhances its reactivity, allowing for further functionalization through cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings. These reactions are instrumental in constructing complex molecular architectures, which are often essential for achieving high binding affinity and selectivity in drug design.

In recent years, the pharmaceutical industry has witnessed a surge in the exploration of indazole derivatives as potential therapeutic candidates. Indazoles, with their fused benzene and pyrazole rings, are known for their broad spectrum of biological activities. Among these, compounds containing the 5-bromo moiety have shown particular promise in the development of antiviral, anticancer, and anti-inflammatory agents. The carboxylate ester group at the 7-position provides an additional handle for further derivatization, enabling the synthesis of a wide array of analogs with tailored pharmacological profiles.

One of the most compelling aspects of Methyl 5-bromo-1H-indazole-7-carboxylate is its utility in the synthesis of kinase inhibitors. Kinases are enzymes that play critical roles in cell signaling pathways, and their dysregulation is often associated with various diseases, including cancer. By leveraging the bromine atom for palladium-catalyzed cross-coupling reactions, researchers can introduce aryl or heteroaryl groups that mimic natural substrates or inhibit kinase activity. This approach has led to the discovery of several potent kinase inhibitors that are currently in clinical development.

The use of Methyl 5-bromo-1H-indazole-7-carboxylate in fragment-based drug design is another area where it has made a significant impact. Fragment-based approaches involve identifying small molecule fragments that bind to target proteins with moderate affinity. These fragments can then be optimized through iterative rounds of chemical modification to produce lead compounds with high efficacy and selectivity. The structural features of Methyl 5-bromo-1H-indazole-7-carboxylate, particularly its bromine substituent, make it an ideal candidate for such strategies.

Recent studies have highlighted the importance of halogenated indazoles in medicinal chemistry. The bromine atom not only serves as a handle for further functionalization but also influences the electronic properties of the molecule, thereby affecting its binding mode to biological targets. For instance, computational studies have shown that halogen bonds can play a crucial role in stabilizing protein-ligand interactions. This has prompted researchers to explore halogenated indazoles as potential scaffolds for designing next-generation drugs with improved pharmacokinetic properties.

The synthesis of Methyl 5-bromo-1H-indazole-7-carboxylate typically involves multi-step organic transformations starting from commercially available precursors. One common synthetic route involves the bromination of an indazole derivative followed by esterification at the carboxyl group. Advances in synthetic methodologies have enabled more efficient and scalable production processes, making this intermediate more accessible to academic and industrial researchers.

The growing interest in biologically active indazole derivatives has spurred innovation in synthetic chemistry. New catalytic systems and reaction conditions have been developed to enhance the efficiency and selectivity of key transformations involved in indazole synthesis. For example, transition-metal-catalyzed C-H activation has emerged as a powerful tool for constructing complex indazole scaffolds directly from simple precursors without the need for pre-functionalized starting materials.

In conclusion, Methyl 5-bromo-1H-indazole-7-carboxylate (CAS No. 898747-24-5) is a versatile and highly valuable intermediate in pharmaceutical synthesis. Its unique structural features and reactivity make it an indispensable tool for medicinal chemists seeking to develop novel therapeutic agents. As research continues to uncover new applications for halogenated indazoles, compounds like this will undoubtedly remain at the forefront of drug discovery efforts.

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