Production Method 1

5332-24-1

898559-24-5

Reaction Conditions

1.1 Reagents: Dilithium dichlorocyanocuprate ,  Magnesate(1-), dichloro[2-methyl-N-(1-methylethyl)-2-propanaminato]-, lithium (1… Solvents: Tetrahydrofuran

Reference

TMP2Mg·2LiCl and related bases for the metalation of unsaturated substrates and the role of the phosphorodiamidate directing group: a new cobalt catalyzed sulfonate, copper exchange

Rohbogner, Christoph, 2010, , ,

Production Method 2

5332-24-1

898559-24-5

Reaction Conditions

1.1 Reagents: Magnesate(1-), dichloro(2,2,6,6-tetramethylpiperidinato)-, lithium (1:1) Solvents: Tetrahydrofuran ;  0.3 h, -30 °C
1.2 Reagents: Iodine Solvents: Tetrahydrofuran
1.3 Solvents: Tetrahydrofuran ;  -30 °C
1.4 Reagents: Ammonium chloride Solvents: Water

Reference

Mixed Mg/Li amides of the type R2NMgCl·LiCl as highly efficient bases for the regioselective generation of functionalized aryl and heteroaryl magnesium compounds

Krasovskiy, Arkady; Krasovskaya, Valeria; Knochel, Paul, Angewandte Chemie, 2006, 45(18), 2958-2961

Production Method 3

5332-24-1

898559-24-5

Reaction Conditions

1.1 Reagents: Magnesate(1-), dichloro[2-methyl-N-(1-methylethyl)-2-propanaminato]-, lithium (1… Solvents: Tetrahydrofuran ;  rt → -25 °C; -25 °C; 3 h, -25 °C
1.2 -
1.3 Reagents: Ammonium chloride Solvents: Water

Reference

New mixed Li/Mg and Li/Mg/Zn amides for the chemoselective metalation of arenes and heteroarenes

Rohbogner, Christoph J.; Wunderlich, Stefan H.; Clososki, Giiuliano C.; Knochel, Paul, European Journal of Organic Chemistry, 2009, (11), 1781-1795

3-Bromoquinoline-2-carbaldehyde Raw materials

• 3-Bromoquinoline

3-Bromoquinoline-2-carbaldehyde Preparation Products

• 3-Bromoquinoline-2-carbaldehyde (898559-24-5)

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Recent Advances in the Application of 3-Bromoquinoline-2-carbaldehyde (CAS: 898559-24-5) in Chemical Biology and Pharmaceutical Research

3-Bromoquinoline-2-carbaldehyde (CAS: 898559-24-5) has emerged as a pivotal scaffold in chemical biology and pharmaceutical research due to its versatile reactivity and potential therapeutic applications. Recent studies have highlighted its role as a key intermediate in the synthesis of bioactive compounds, particularly in the development of kinase inhibitors and antimicrobial agents. This research brief consolidates the latest findings on the synthesis, mechanistic insights, and biological activities associated with this compound, providing a comprehensive overview for researchers in the field.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the efficacy of 3-Bromoquinoline-2-carbaldehyde derivatives as selective inhibitors of cyclin-dependent kinases (CDKs), which are critical targets in cancer therapy. The research team employed structure-activity relationship (SAR) analysis to optimize the substitution patterns on the quinoline core, leading to compounds with improved potency and selectivity. Notably, the bromo-substituent at the 3-position was found to enhance binding affinity through halogen bonding interactions with the kinase active site.

In the realm of antimicrobial research, a recent investigation in Bioorganic & Medicinal Chemistry Letters reported the synthesis of novel 3-Bromoquinoline-2-carbaldehyde Schiff bases exhibiting potent activity against drug-resistant Staphylococcus aureus strains. The study revealed that the aldehyde functionality serves as a crucial pharmacophore, enabling the formation of imine linkages with various amines to generate libraries of bioactive compounds. Molecular docking studies further elucidated the binding modes of these derivatives with bacterial target proteins.

From a synthetic chemistry perspective, advancements in the preparation of 3-Bromoquinoline-2-carbaldehyde have been achieved through palladium-catalyzed cross-coupling reactions, as detailed in a 2024 Organic Process Research & Development publication. The optimized protocol features improved atom economy and reduced environmental impact compared to traditional bromination methods. These methodological improvements have significant implications for the scalable production of quinoline-based pharmaceuticals.

The compound's potential in neurodegenerative disease research has also gained attention. A recent ACS Chemical Neuroscience study demonstrated that 3-Bromoquinoline-2-carbaldehyde derivatives can modulate α-synuclein aggregation, suggesting possible applications in Parkinson's disease therapeutics. The researchers identified specific structural modifications that enhance blood-brain barrier penetration while maintaining activity against protein misfolding.

Looking forward, the unique chemical properties of 3-Bromoquinoline-2-carbaldehyde (CAS: 898559-24-5) continue to inspire innovative applications across multiple therapeutic areas. Current research directions include the development of fluorescent probes for biological imaging and the design of proteolysis targeting chimeras (PROTACs) for targeted protein degradation. These emerging applications underscore the compound's enduring relevance in cutting-edge pharmaceutical research.

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