2549-19-1

Basic information

• Product Name: 2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: 2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER;ETHYL 2-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLATE;BUTTPARK 9\05-51;Ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate ,97%;2-Methyl-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester ,97%;2-Methyl-iMidazo[1,2-a]pyridin-3-carboxylic acid ethyl ester;ethyl 2-MethylH-iMidazo[1,2-a]pyridine-3-carboxylate;Ethyl 2-MethyliMidazo[1,2-a]pyridine-3-carboxylate, tech. 90%
• CAS NO: 2549-19-1
• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 204.23
• Mol File: 2549-19-1.mol
• Article Data: 20

Chemical Properties

• Melting Point: 64-65 °C
• Appearance: /
• Density: 1.19±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 5.29±0.10(Predicted)
• CAS DataBase Reference: 2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER(2549-19-1)
• EPA Substance Registry System: 2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER(2549-19-1)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/38
• Safety Statements: 24/25-36/37/39
• Hazardous Substances Data: 2549-19-1(Hazardous Substances Data)

Usage

Description

2-Methyl-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester, also known as Ethyl 2-Methylimidazo[1,2-a]pyridine-3-carboxylate, is an organic compound with a light yellow to brown solid appearance. It is characterized by its unique chemical structure, which contributes to its various applications in the field of chemistry and pharmaceuticals.

Uses

Used in Chemical Synthesis:
2-Methyl-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester is used as a synthetic intermediate for the preparation of β-hydroxy carbonyl compounds and α,β-unsaturated carbonyl compounds. Its unique structure allows for the creation of a wide range of chemical products, making it a valuable compound in the field of organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Methyl-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester is utilized as a key component in the development of various drugs. Its versatility in chemical synthesis enables the creation of new drug candidates with potential therapeutic applications.
Used in Research and Development:
2-Methyl-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester is also employed in research and development settings, where it is used to study the properties and reactions of similar compounds. This helps scientists and researchers to better understand the behavior of these molecules and develop new strategies for their application in various industries.

Synthesis Reference(s)

The Journal of Organic Chemistry, 30, p. 2403, 1965 DOI: 10.1021/jo01018a071

Upstream product

• 141-97-9 ethyl acetoacetate 
• 504-29-0 2-aminopyridine 
• 110-86-1 pyridine 
• 95239-03-5 tert-butyl 2-(4-ethoxy-4-oxobut-2-en-2-yl)diazene-1-carboxylate 
• 36171-99-0 N₁,N₁-dimethyl-N₂-pyridyl-2'-acetamidine 
• 105-36-2 ethyl bromoacetate 
• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 
• 84911-18-2 ethyl 2-bromoacetoacetate 

Downstream Products

• 331638-05-2 2-methyl-N-(3-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide 
• 477852-38-3 N-(4-chlorophenyl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 357160-94-2 N-(4-bromophenyl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 329715-90-4 N-cyclohexyl-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 903744-27-4 2-methyl-N-phenethylimidazo[1,2-a]pyridine-3-carboxamide 
• 352024-12-5 N-benzyl-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 62772-71-8 2-methyl-N-phenylimidazo[1,2-a]pyridine-3-carboxamide 
• 155699-17-5 2-methyl-N'-(4-methylbenzylidene)imidazo[1,2-a]pyridine-3-carbohydrazide 
• 359646-90-5 2-methyl-N'-(3,4,5-trimethoxybenzylidene)imidazo[1,2-a]pyridine-3-carbohydrazide 
• 331426-82-5 N'-(4-(benzyloxy)benzylidene)-2-methylimidazo[1,2-a]pyridine-3-carbohydrazide 
• 359822-95-0 N'-(4-hydroxybenzylidene)-2-methylimidazo[1,2-a]pyridine-3-carbohydrazide 
• 1621321-41-2 2-methyl-N'-(4-(trifluoromethyl)benzylidene)imidazo[1,2-a]pyridine-3-carbohydrazide 
• 209471-05-6 N'-(4-bromobenzylidene)-2-methylimidazo[1,2-a]pyridine-3-carbohydrazide 
• 1621321-40-1 2-methyl-N'-(4-phenoxybenzoyl)imidazo[1,2-a]pyridine-3-carbohydrazide 

Relevant articles and documents

Synthesis and biological evaluation of new imidazo[1,2-a]pyridine derivatives designed as mefloquine analogues.

This paper describes the synthesis and the in vitro antimalarial profile of two new imidazo[1,2-a]pyridine derivatives 4HCl and 13HCl, structurally proposed as mefloquine (1) analogues, by exploring bioisosterism and molecular simplification tools. The synthetic route employed to access the title compounds used, as starting material, the previously described ethyl 2-methylimidazo[1,2-aJpyridine-3-carboxylate derivative (5). These novel heterocyclic derivatives 4HCl and 13HCl presented modest antimalarial activity against the W-2 and D-6 clones of Plasmodium falciparum as well as inhibitors of in vitro heme polymerization compared to mefloquine.

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

A facile and environmental friendly protocol for the synthesis of N-bridged fused bicyclic compounds such as imidazo[1,2-a]pyridines, imidazo[1,2-a]pyrimidines, and imidazo[2,1-b]thiazole, from commercially available starting materials has been developed.

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

A wide range of imidazo[1,2-a]pyridines are accessible from cheap and readily available 2-aminopyridines and 1,3-dicarbonyl compounds using a unique CBrCl3/2-aminopyridine system for bromination at the α-carbon. 2-Aminopyridine is not only the substrate but also acts as a bromination shuttle, transferring the bromine atom from CBrCl3 to the α-carbon of the 1,3-dicarbonyl. The reaction mechanism involves a series of reversible steps, including an addition reaction with cyclic transition state, to form a bromo-hemiaminal intermediate. Isolated yields of up to 97% were obtained under mild conditions and at short reaction times in this transition metal-free, one-pot synthesis.