6-bromo-4-methoxy-1H-indazole

6-Bromo-4-methoxy-1H-indazole (CAS: 885519-21-1) is a bromo-substituted indazole heterocycle widely used as an important intermediate in chemical and pharmaceutical research. Below is a detailed overview of its functions and applications:

🧪 1. Chemical Uses

1. Pharmaceutical Intermediate

   • This compound is commonly used in the optimization of new drug molecules, especially in the design of kinase inhibitors, anticancer drugs, anti-inflammatory agents, and CNS-active compounds.

   • The indazole ring is a key scaffold in many drugs, such as:

     • Indazole-based tyrosine kinase inhibitors (e.g., Vemurafenib, Tivantinib)

     • PDE inhibitors (used in cardiovascular or antidepressant research)

   • The 6-bromo substitution provides an active site for further functionalization, suitable for coupling reactions such as Suzuki, Sonogashira, and Buchwald–Hartwig to generate various derivatives.

2. Organic Synthesis Reagent

   • Serves as an intermediate for heterocyclic substitution reactions in the synthesis of complex molecules, materials chemistry, and polymer studies.

   • The bromine atom’s reactivity allows it to act as a substrate in cross-coupling reactions, enabling the introduction of new aryl or alkyl groups.

⚗️ 2. Role in Research and Drug Discovery

• Used in lead compound discovery to construct small-molecule libraries.

• Important for Structure–Activity Relationship (SAR) studies to analyze electronic and steric effects.

• Some reported derivatives show potential biological activities such as:

  • Antitumor effects (by inhibiting BRAF, PI3K, etc.)

  • Anti-inflammatory activity

  • CNS modulation properties

⚙️ 3. Applications in Materials and Optoelectronics (Secondary Use)

• Indazole derivatives have applications in OLED emitting materials and organic semiconductors, due to their conjugated structure and stability.

• The bromo-substituted structure facilitates coupling reactions to build extended π-conjugated systems.

📋 Summary