Methyl 1-methyl-1H-imidazo[4,5-c]pyridine-2-carboxylate
[CAS# 1566797-32-7]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Methyl 1-methyl-1H-imidazo[4,5-c]pyridine-2-carboxylate
• Molecular Formula: C₉H₉N₃O₂
• Molecular Weight: 191.19
• CAS Registry Number: 1566797-32-7
• SMILES: COC(=O)c1nc2cnccc2n1C

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Boiling point: 356.4±34.0 ºC 760 mmHg (Calc.)^*
• Flash point: 169.4±25.7 ºC (Calc.)^*
• Index of refraction: 1.631 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovory and Applicatios

Methyl 1-methyl-1H-imidazo[4,5-c]pyridine-2-carboxylate is a heterocyclic compound consisting of a fused imidazole and pyridine ring system, substituted with a methyl group at the N1 position and a carboxylate ester at the second position. The imidazo[4,5-c]pyridine scaffold represents a class of bicyclic heterocycles widely recognized for their biological and chemical versatility. Incorporation of a methyl group on the nitrogen atom can influence electronic properties and steric profile, while the ester functionality provides a handle for further chemical modification, enabling synthesis of amides, acids, or more complex derivatives.

The synthesis of methyl 1-methyl-1H-imidazo[4,5-c]pyridine-2-carboxylate typically involves cyclization of appropriately substituted aminopyridine precursors with reagents that introduce the imidazole ring. Alkylation at the N1 position is often performed prior to or after cyclization, depending on the chosen synthetic route, to ensure selective methylation. The carboxylate group is introduced through esterification of the corresponding carboxylic acid, which may be obtained directly in the cyclization step or via oxidation of an aldehyde precursor. Purification is commonly achieved by recrystallization or chromatography to yield a well-defined crystalline product.

In synthetic chemistry, this compound serves as a versatile intermediate for constructing substituted imidazo[4,5-c]pyridine derivatives. The ester group can be hydrolyzed to afford the carboxylic acid, which may then be converted into amides, hydrazides, or other derivatives suitable for medicinal chemistry applications. The heterocyclic nitrogen atoms can participate in electrophilic or nucleophilic reactions, allowing the introduction of additional substituents at specific positions on the bicyclic scaffold. This combination of functional groups provides a platform for modular synthesis and chemical diversification.

In medicinal chemistry, derivatives of methyl 1-methyl-1H-imidazo[4,5-c]pyridine-2-carboxylate are explored for their potential as enzyme inhibitors, receptor modulators, and bioactive agents. The planar heterocyclic structure allows π–π stacking and hydrogen bonding with protein targets, while substituents at the nitrogen and carboxylate positions enable fine-tuning of binding affinity, solubility, and pharmacokinetic properties. Systematic modifications of this scaffold have been employed to optimize interactions with biological targets and improve overall pharmacological performance.

The compound is also utilized in chemical research and methodology development. Its functionalized bicyclic system allows the study of selective alkylation, esterification, and heterocycle functionalization reactions. Researchers can explore reactivity patterns of fused imidazole–pyridine systems, evaluate regioselectivity in functionalization, and develop novel synthetic routes toward more complex heterocycles. Additionally, the compound can be used as a building block in combinatorial synthesis for generating small molecule libraries.

Physically, methyl 1-methyl-1H-imidazo[4,5-c]pyridine-2-carboxylate is typically obtained as a solid with moderate solubility in polar organic solvents such as dimethylformamide, ethanol, and dichloromethane. It is generally stable under ambient laboratory conditions but should be protected from strong acids, bases, and oxidizing agents that may compromise the ester or the heterocyclic core. Proper storage ensures its integrity for synthetic and medicinal applications.

Overall, methyl 1-methyl-1H-imidazo[4,5-c]pyridine-2-carboxylate is a chemically versatile fused heterocycle with functional groups that allow selective transformations and derivatization. Its methylated nitrogen, carboxylate ester, and imidazo[4,5-c]pyridine core provide a platform for the synthesis of bioactive compounds, heterocyclic derivatives, and functional intermediates in both medicinal and synthetic organic chemistry.