Production Method 1

552331-16-5

14874-70-5

43625-65-6

878064-16-5

Reaction Conditions

1.1 Solvents: Ethyl acetate ;  5 h, rt

Reference

Amine-free melanin-concentrating hormone receptor 1 antagonists: Novel non-basic 1-(2H-indazole-5-yl)pyridin-2(1H)-one derivatives and mitigation of mutagenicity in Ames test

Igawa, Hideyuki; et al, Bioorganic & Medicinal Chemistry, 2016, 24(11), 2504-2518

Production Method 2

465529-56-0

878064-16-5

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  -78 °C; 10 min, 0 - 5 °C; 5 °C → -78 °C
1.2 12 h, 25 °C

Reference

Discovery of N-(4-(3-isopropyl-2-methyl-2H-indazol-5-yl)pyrimidin-2-yl)-4-(4-methylpiperazin-1-yl)quinazolin-7-amine as a Novel, Potent, and Oral Cyclin-Dependent Kinase Inhibitor against Haematological Malignancies

Huang, Jianhang; et al, Journal of Medicinal Chemistry, 2021, 64(17), 12548-12571

Production Method 3

465529-56-0

878064-16-5

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  -78 °C; 15 min, 0 - 5 °C
1.2 overnight, -78 °C; -78 °C → rt

Reference

Convenient method for the 3-functionalization of isoindazoles

Bunnell, Aaron; et al, Synthetic Communications, 2006, 36(3), 285-293

Production Method 4

465529-55-9

878064-16-5

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  0 °C; 30 min, rt
1.2 rt
1.3 Solvents: Water ;  0 °C
2.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  -78 °C; 10 min, 0 - 5 °C; 5 °C → -78 °C
2.2 12 h, 25 °C

Reference

Discovery of N-(4-(3-isopropyl-2-methyl-2H-indazol-5-yl)pyrimidin-2-yl)-4-(4-methylpiperazin-1-yl)quinazolin-7-amine as a Novel, Potent, and Oral Cyclin-Dependent Kinase Inhibitor against Haematological Malignancies

Huang, Jianhang; et al, Journal of Medicinal Chemistry, 2021, 64(17), 12548-12571

Production Method 5

552331-16-5

878064-16-5

552331-30-3

Reaction Conditions

1.1 Reagents: Cesium carbonate

Reference

Discovery and characterization of N-(1,3-dialkyl-1H-indazol-6-yl)-1H-pyrazolo[4,3-b]pyridin-3-amine scaffold as mGlu4 positive allosteric modulators that mitigate CYP1A2 induction liability

Engers, Darren W.; et al, Bioorganic & Medicinal Chemistry Letters, 2018, 28(15), 2641-2646

Production Method 6

552331-16-5

4637-24-5

878064-16-5

552331-30-3

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  rt; 18 h, 90 °C

Reference

Selective methylation of NH-containing heterocycles and sulfonamides using N,N-dimethylformamide dimethylacetal based on calculated pKa measurements

Fairley, Gary; et al, Synlett, 2013, 24(5), 570-574

5-Bromo-2,3-dimethyl-2H-indazole Raw materials

• 5-Bromo-3-methyl-1H-indazole
• (dimethoxymethyl)dimethylamine
• Borate(1-),tetrafluoro-
• Oxonium, trimethyl-(9CI)
• 5-Bromo-2-methyl-2H-indazole
• 5-BROMO-1H-INDAZOLE

5-Bromo-2,3-dimethyl-2H-indazole Preparation Products

• 5-Bromo-1,3-dimethyl-1H-indazole (552331-30-3)
• 5-Bromo-2,3-dimethyl-2H-indazole (878064-16-5)

• 1. Excess electrons in lithium–ethylamine solutions—density, electrical conductivity and EPR studies
  Phys. Chem. Chem. Phys., 1999,1, 3561-3565
• 2. Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration?
  Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755
• 3. Evidence for the intrinsic nature of band-gap states electrochemically observed on atomically flat TiO2(110) surfaces?
  Shintaro Takata,Yoshihiro Miura Phys. Chem. Chem. Phys., 2014,16, 24784-24789
• 4. Enabling high-throughput single-animal gene-expression studies with molecular and micro-scale technologies
  Jason Wan Lab Chip, 2020,20, 4528-4538
• 5. Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials?
  Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-Garayoa RSC Adv., 2017,7, 24133-24139

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzopyrazoles Indazoles

Recent Advances in the Study of 5-Bromo-2,3-dimethyl-2H-indazole (CAS: 878064-16-5) in Chemical Biology and Pharmaceutical Research

The compound 5-Bromo-2,3-dimethyl-2H-indazole (CAS: 878064-16-5) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. As a brominated indazole derivative, this molecule serves as a versatile scaffold for the development of novel bioactive compounds. Recent studies have explored its role as a key intermediate in the synthesis of kinase inhibitors, anticancer agents, and anti-inflammatory drugs, highlighting its broad utility in drug discovery.

One of the most notable advancements in the study of 5-Bromo-2,3-dimethyl-2H-indazole is its application in the design of selective kinase inhibitors. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives of this compound exhibit potent inhibitory activity against cyclin-dependent kinases (CDKs), particularly CDK2 and CDK9. The researchers utilized structure-activity relationship (SAR) analysis to optimize the bromo and methyl substituents, resulting in compounds with improved selectivity and pharmacokinetic profiles. These findings suggest that 5-Bromo-2,3-dimethyl-2H-indazole derivatives could serve as promising candidates for targeted cancer therapies.

In addition to its role in kinase inhibition, recent research has investigated the anti-inflammatory potential of 5-Bromo-2,3-dimethyl-2H-indazole. A study published in Bioorganic & Medicinal Chemistry Letters (2024) reported that this compound and its analogs effectively suppress the production of pro-inflammatory cytokines, such as TNF-α and IL-6, in macrophage cell lines. Mechanistic studies revealed that these effects are mediated through the modulation of the NF-κB signaling pathway, positioning 5-Bromo-2,3-dimethyl-2H-indazole as a potential lead compound for the development of new anti-inflammatory drugs.

The synthetic utility of 5-Bromo-2,3-dimethyl-2H-indazole has also been a focus of recent investigations. A 2024 paper in Organic & Biomolecular Chemistry described an efficient, one-pot synthesis method for this compound, utilizing palladium-catalyzed cross-coupling reactions. This approach not only improves the yield and purity of the product but also reduces the environmental impact of the synthesis process, aligning with the principles of green chemistry. Such advancements in synthetic methodology are critical for scaling up production and facilitating further pharmacological studies.

Despite these promising developments, challenges remain in the clinical translation of 5-Bromo-2,3-dimethyl-2H-indazole-based therapeutics. Issues such as bioavailability, metabolic stability, and off-target effects need to be addressed through comprehensive preclinical studies. However, the growing body of research underscores the potential of this compound as a valuable tool in chemical biology and a foundation for innovative drug design. Future studies are expected to explore its applications in other therapeutic areas, such as neurodegenerative diseases and infectious diseases, further expanding its impact on pharmaceutical research.

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