Production Method 1

19798-81-3

921-03-9

878197-68-3

Reaction Conditions

1.1 Solvents: 1,2-Dimethoxyethane ;  25 °C; 25 °C → 65 °C; 2 - 4 h, 65 °C; 65 °C → 10 °C; 1 h, 10 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  10 °C; 10 °C → 75 °C; 16 - 20 h, 75 °C; 75 °C → 10 °C
1.3 Reagents: Sodium hydroxide Solvents: Water ;  pH 8, 10 °C

Reference

Kilogram-Scale Synthesis of the CXCR4 Antagonist GSK812397

Boggs, Sharon; Elitzin, Vassil I.; Gudmundsson, Kristjan; Martin, Michael T.; Sharp, Matthew J., Organic Process Research & Development, 2009, 13(4), 781-785

5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde Raw materials

• 6-Bromopyridin-2-amine
• 1,1,3-Trichloroacetone

5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde Preparation Products

• 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde (878197-68-3)

• 1. Emerging enantiomeric resolution materials with homochiral nano-fabrications
  Ji-Ping Wei Nanoscale, 2015,7, 11815-11832
• 2. Fate of Sb(v) and Sb(iii) species along a gradient of pH and oxygen concentration in the Carnoulès mine waters (Southern France)
  Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique Desoeuvre Environ. Sci.: Processes Impacts, 2013,15, 1536-1544
• 3. Dissociation of aryl sulfonyl phthalimide radical anions: relevance to the biological activity of arylsulfonyl amides?
  Abdelaziz Houmam,Emad M. Hamed Chem. Commun., 2012,48, 11328-11330
• 4. Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements
  Analyst, 1991,116, 1125-1130
• 5. Exchangeability of amino acid residues with similar physicochemical properties in coiled-coil interactions?
  Guiying Zhang,Maosheng Cheng,Yanni Li,Keliang Liu,Lifeng Cai Chem. Commun., 2013,49, 11086-11088

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Imidazopyridines Imidazopyridines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Imidazopyridines

Comprehensive Overview of 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde (CAS No. 878197-68-3)

5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde (CAS No. 878197-68-3) is a highly specialized organic compound that has garnered significant attention in pharmaceutical and agrochemical research. This brominated heterocyclic aldehyde is a key intermediate in the synthesis of various bioactive molecules, particularly those targeting kinase inhibitors and antimicrobial agents. Its unique imidazo[1,2-a]pyridine scaffold makes it a valuable building block in medicinal chemistry, aligning with current trends in drug discovery and small molecule therapeutics.

The compound's structural features, including the 5-bromo substituent and the aldehyde functional group, contribute to its reactivity and versatility in organic synthesis. Researchers are increasingly exploring its potential in catalyzed cross-coupling reactions, a hot topic in modern green chemistry and sustainable synthesis. This aligns with frequent search queries about eco-friendly chemical processes and atom-efficient transformations in scientific databases.

In the context of structure-activity relationship (SAR) studies, 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde serves as a crucial precursor for developing compounds with improved pharmacokinetic properties. Recent publications highlight its use in designing selective enzyme modulators, addressing common search terms like targeted drug design and precision medicine approaches. The compound's electron-deficient aromatic system makes it particularly interesting for molecular docking studies and virtual screening applications.

From a synthetic chemistry perspective, the aldehyde functionality in this molecule allows for diverse nucleophilic addition reactions, making it valuable for creating molecular libraries in combinatorial chemistry. This aspect responds to frequent industry searches about high-throughput screening and lead compound optimization. The bromine atom at the 5-position offers excellent opportunities for palladium-catalyzed transformations, a subject of numerous recent patents and research papers.

Quality control of 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde typically involves advanced analytical techniques such as HPLC purity analysis, mass spectrometry, and NMR spectroscopy, addressing common quality-related search terms in the chemical industry. The compound's stability profile and storage conditions are frequently discussed topics in technical forums, especially regarding its sensitivity to oxidation and light exposure.

In material science applications, this compound has shown promise in the development of organic electronic materials, particularly as a precursor for conjugated polymers with potential applications in optoelectronic devices. This connects with trending searches about next-generation materials and energy-efficient technologies.

The global market for 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde reflects growing demand from contract research organizations and pharmaceutical developers, with particular interest from regions investing heavily in biotech innovation. Supply chain considerations often include discussions about scalable synthesis routes and regulatory compliance, which are common concerns in chemical procurement searches.

Recent advancements in flow chemistry have opened new possibilities for the efficient production of this compound, addressing industry pain points about process intensification and waste reduction. These developments align with the increasing focus on green chemistry metrics in academic and industrial research.

From a safety perspective, proper handling of 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde requires standard laboratory precautions, with particular attention to its aldehyde group reactivity. This responds to frequent queries about chemical handling protocols and laboratory safety measures in research settings.

The compound's role in medicinal chemistry continues to expand, with recent studies exploring its derivatives as potential anti-inflammatory agents and central nervous system modulators. These applications connect with trending healthcare searches about novel therapeutic approaches for chronic diseases.

In conclusion, 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde (CAS No. 878197-68-3) represents a versatile and valuable chemical entity with broad applications across multiple scientific disciplines. Its importance in contemporary research is reflected in the growing body of literature and patent filings referencing this compound, making it a subject of ongoing interest in both academic and industrial chemistry communities.

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