Production Method 1

105-45-3

943112-78-5

Reaction Conditions

1.1 Reagents: Bromotrichloromethane ,  Potassium bicarbonate Solvents: Acetonitrile ;  5 h, 80 °C

Reference

2-Aminopyridines as an α-Bromination Shuttle in a Transition Metal-Free One-Pot Synthesis of Imidazo[1,2-a]pyridines

Roslan, Irwan Iskandar; Ng, Kian-Hong; Chuah, Gaik-Khuan; Jaenicke, Stephan, Advanced Synthesis & Catalysis, 2016, 358(3), 364-369

Production Method 2

105-45-3

943112-78-5

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Polyethylene glycol ;  5 min, rt; 1 h, 80 °C

Reference

Sonochemical Synthesis and In Silico Evaluation of Imidazo[1,2-a]Pyridine Derivatives as Potential Inhibitors of Sirtuins

Ramarao, Sidda; Pothireddy, Mohanreddy; Venkateshwarlu, Rapolu; Moturu, Krishna Murthy V. R.; Siddaiah, Vidavalur; et al, Polycyclic Aromatic Compounds, 2023, 43(4), 3741-3760

Production Method 3

609-15-4

943112-78-5

Reaction Conditions

1.1 Solvents: Ethanol ;  20 h, reflux

Reference

Design, Synthesis, and Pharmacological Evaluation of N-Acylhydrazones and Novel Conformationally Constrained Compounds as Selective and Potent Orally Active Phosphodiesterase-4 Inhibitors

Kummerle, Arthur E.; Schmitt, Martine; Cardozo, Suzana V. S.; Lugnier, Claire; Villa, Pascal; et al, Journal of Medicinal Chemistry, 2012, 55(17), 7525-7545

Production Method 4

105-45-3

943112-78-5

Reaction Conditions

1.1 Reagents: tert-Butyl hydroperoxide Catalysts: Boron trifluoride etherate ,  Tetrabutylammonium iodide Solvents: Acetonitrile ;  9 h, 80 °C

Reference

TBAI-catalyzed oxidative coupling of aminopyridines with β-keto esters and 1,3-diones - synthesis of imidazo[1,2-a]pyridines

Ma, Lijuan; Wang, Xianpei; Yu, Wei; Han, Bing, Chemical Communications (Cambridge, 2011, 47(40), 11333-11335

Production Method 5

943112-78-5

Reaction Conditions

Reference

Thermal and microwave-assisted rapid syntheses of substituted imidazo[1,2-a]pyridines under solvent- and catalyst-free conditions [Erratum to document cited in CA154:588804]

Chunavala, Kaushik C.; Joshi, Girdhar; Suresh, Eringathodi; Adimurthy, Subbarayappa, Synthesis, 2011, (8),

Production Method 6

105-45-3

943112-78-5

Reaction Conditions

1.1 Reagents: Carbon tetrabromide Solvents: Acetonitrile ;  3 - 36 h, 80 °C

Reference

CBr4 Mediated Oxidative C-N Bond Formation: Applied in the Synthesis of Imidazo[1,2-α]pyridines and Imidazo[1,2-α]pyrimidines

Huo, Congde; Tang, Jing; Xie, Haisheng; Wang, Yajun; Dong, Jie, Organic Letters, 2016, 18(5), 1016-1019

Production Method 7

3600-18-8

943112-78-5

Reaction Conditions

1.1 rt; 10 min, 55 °C
1.2 Reagents: Sodium sulfite Solvents: Water ;  pH 8 - 9

Reference

Thermal and microwave-assisted rapid syntheses of substituted imidazo[1,2-a]pyridines under solvent- and catalyst-free conditions

Chunavala, Kaushik C.; Joshi, Girdhar; Suresh, Eringathodi; Adimurthy, Subbarayappa, Synthesis, 2011, (4), 635-641

Production Method 8

4755-81-1

943112-78-5

Reaction Conditions

1.1 Solvents: Methanol ;  overnight, rt

Reference

Synthesis and characterisation of novel N substituted 2-methylimidazo[1,2a]pyridine-3-carboxamides

Han, Tao; Shi, Zhichuan; Peng, Yongle; Zhao, Zhigang, Journal of Chemical Research, 2011, 35(4), 243-245

Production Method 9

105-45-3

943112-78-5

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Water ;  30 min, 80 °C
1.2 30 min, 80 °C

Reference

NBS mediated protocol for the synthesis of N-bridged fused heterocycles in water

Bhagat, Saket B.; Telvekar, Vikas N., Tetrahedron Letters, 2017, 58(37), 3662-3666

Production Method 10

95239-02-4

943112-78-5

Reaction Conditions

1.1 3.5 h, rt

Reference

A Novel Solvent-Free Approach to Imidazole Containing Nitrogen-Bridgehead Heterocycles

Attanasi, Orazio A.; Bianchi, Luca; Campisi, Linda A.; De Crescentini, Lucia; Favi, Gianfranco; et al, Organic Letters, 2013, 15(14), 3646-3649

Production Method 11

105-45-3

943112-78-5

Reaction Conditions

1.1 Reagents: Potassium bicarbonate Solvents: Acetonitrile ,  Bromotrichloromethane ;  10 h, rt

Reference

Synthesis of Disubstituted 3-Phenylimidazo[1,2-a]pyridines via a 2-Aminopyridine/CBrCl3 α-Bromination Shuttle

Roslan, Irwan Iskandar; Ng, Kian-Hong; Wu, Ji'-En; Chuah, Gaik-Khuan; Jaenicke, Stephan, Journal of Organic Chemistry, 2016, 81(19), 9167-9174

Production Method 12

105-45-3

943112-78-5

Reaction Conditions

1.1 Reagents: Potassium bromide Catalysts: Erythrosine Solvents: Acetonitrile ;  24 h, rt

Reference

Photocatalytic regeneration of brominating agent in the visible light-mediated synthesis of imidazo[1,2-a]pyridines

Roslan, Irwan Iskandar; Ng, Kian-Hong; Jaenicke, Stephan; Chuah, Gaik-Khuan, Catalysis Science & Technology, 2019, 9(6), 1528-1534

Production Method 13

105-45-3

943112-78-5

Reaction Conditions

1.1 Reagents: Iodobenzene diacetate Catalysts: Boron trifluoride etherate Solvents: Tetrahydrofuran ;  overnight, 7 °C

Reference

Synthesis of imidazo[1,2-a]pyridines by the bis(acetyloxy)(phenyl)-λ3-iodane-mediated oxidative coupling of 2-aminopyridines with β-keto esters and 1,3-diones

Wang, Xianpei; Ma, Lijuan; Yu, Wei, Synthesis, 2011, (15), 2445-2453

Methyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate Raw materials

• Methyl 2-chloroacetoacetate
• Ethyl 2-chloroacetoacetate
• Diazenecarboxylic acid, (3-methoxy-1-methyl-3-oxo-1-propenyl)-,1,1-dimethylethyl ester
• Methyl 2-bromo-3-oxobutanoate
• methyl 3-oxobutanoate

Methyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate Preparation Products

• Methyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate (943112-78-5)

• 1. Acetyl group orientation modulates the electronic ground-state asymmetry of the special pair in purple bacterial reaction centers
  P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. Buda Phys. Chem. Chem. Phys., 2011,13, 10270-10279
• 2. An assessment of strategies for the development of solid-state adsorbents for vehicular hydrogen storage
  Mark D. Allendorf,Alauddin Ahmed,Tom Autrey,Jeffrey Camp,Eun Seon Cho,Maciej Haranczyk,Abhi Karkamkar,Di-Jia Liu,Katie R. Meihaus,Iffat H. Nayyar,Roman Nazarov,Donald J. Siegel,Vitalie Stavila,Jeffrey J. Urban,Srimukh Prasad Veccham,Brandon C. Wood Energy Environ. Sci., 2018,11, 2784-2812
• 3. An anti-leakage liquid metal thermal interface material
  Kaiyuan Huang,Wangkang Qiu,Meilian Ou,Xiaorui Liu,Zenan Liao,Sheng Chu RSC Adv., 2020,10, 18824-18829
• 4. An atomistic mechanism for the degradation of perovskite solar cells by trapped charge?
  Eunhak Lim,Jiyoung Heo,Seong Keun Kim Nanoscale, 2019,11, 11369-11378
• 5. An integrated process of CO2 capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system?
  Yu-Nong Li,Liang-Nian He,Xian-Dong Lang,Xiao-Fang Liu,Shuai Zhang RSC Adv., 2014,4, 49995-50002

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

Methyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate (CAS No. 943112-78-5): A Comprehensive Overview

Methyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate (CAS No. 943112-78-5) is a versatile compound with significant potential in the fields of medicinal chemistry and pharmaceutical research. This compound, characterized by its unique structural features, has garnered attention for its diverse biological activities and potential therapeutic applications.

The chemical structure of Methyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate consists of a methyl ester group attached to a 2-methylimidazo[1,2-a]pyridine core. This core structure is known for its ability to interact with various biological targets, making it a valuable scaffold for the development of novel drugs. Recent studies have highlighted the importance of this scaffold in the design of compounds with improved pharmacological properties.

In the realm of medicinal chemistry, Methyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate has been investigated for its potential as a lead compound in the development of drugs targeting specific diseases. For instance, research has shown that derivatives of this compound exhibit potent anti-inflammatory and anti-cancer activities. These findings have opened new avenues for the exploration of this chemical class in drug discovery and development.

One of the key areas where Methyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate has shown promise is in the treatment of inflammatory disorders. Inflammatory diseases, such as rheumatoid arthritis and inflammatory bowel disease, are characterized by chronic inflammation and tissue damage. Studies have demonstrated that compounds derived from Methyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate can effectively modulate inflammatory pathways, thereby reducing inflammation and associated symptoms.

Beyond its anti-inflammatory properties, Methyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate has also been explored for its anti-cancer potential. Cancer remains a leading cause of mortality worldwide, and the development of new therapeutic agents is crucial. Research has shown that certain derivatives of this compound can selectively target cancer cells while sparing healthy cells. This selective cytotoxicity makes it an attractive candidate for further investigation in oncology.

The pharmacokinetic properties of Methyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate are another area of interest. Understanding how this compound is absorbed, distributed, metabolized, and excreted in the body is essential for optimizing its therapeutic potential. Recent studies have provided valuable insights into these processes, highlighting the importance of careful formulation and dosing strategies to maximize efficacy and minimize side effects.

In addition to its biological activities, the synthetic accessibility of Methyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate is a significant advantage. The ability to synthesize this compound efficiently and on a large scale is crucial for advancing its development as a pharmaceutical agent. Chemists have developed various synthetic routes to produce this compound with high yields and purity, ensuring a reliable supply for research and clinical trials.

The safety profile of Methyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate is also an important consideration. Preclinical studies have generally shown favorable safety profiles for this compound and its derivatives. However, ongoing research is necessary to fully understand any potential toxicities or adverse effects that may arise during long-term use or at higher doses.

In conclusion, Methyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate (CAS No. 943112-78-5) represents a promising chemical entity with diverse biological activities and potential therapeutic applications. Its unique structural features and favorable pharmacological properties make it an attractive candidate for further investigation in drug discovery and development. As research continues to advance our understanding of this compound, it holds significant potential to contribute to the treatment of various diseases and improve patient outcomes.

• 2549-19-1(Ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate)
• 123531-52-2(Ethyl imidazo1,2-apyridine-3-carboxylate)
• 1038828-20-4(3-methyl-Imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester)
• 81438-51-9(Ethyl 2,6-Dimethylimidazo1,2-Apyridine-3-carboxylate)
• 1400766-07-5(Ethyl 3,6-dimethylimidazo[1,2-a]pyridine-2-carboxylate)
• 1220397-13-6(Methyl Imidazo1,2-apyridine-2-carboxylate)
• 81448-48-8(Ethyl 2,7-dimethylimidazo1,2-apyridine-3-carboxylate)
• 62772-68-3(Imidazo[1,2-a]pyridine-3-carboxylic acid, 2-methyl-, ethyl ester,monohydrochloride)
• 1400766-01-9(3,7-dimethyl-Imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester)
• 1400766-19-9(3,5-dimethyl-Imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester)