Imidazo[1,2-a]pyridine

Base Information

• Chemical Name: Imidazo[1,2-a]pyridine
• CAS No.: 274-76-0
• Molecular Formula: C7H6N2
• Molecular Weight: 118.138
• Hs Code.: 29339900
• Mol file: 274-76-0.mol

Synonyms:1,3a-Diazaindene;1-Azaindolizine;Pyridino[1',2':1,2]glyoxaline;Pyrimidazole;

Chemical Property of Imidazo[1,2-a]pyridine

Chemical Property:

• Refractive Index: n20/D 1.626(lit.)
• Boiling Point: 103oC (1 mmHg)
• PKA: 6.80±0.30(Predicted)
• Flash Point: 113oC
• PSA: 17.30000
• Density: 1.142 g/cm³
• LogP: 1.33430
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform, Methanol

Purity/Quality:

99% ^*data from raw suppliers

Imidazo[1,2-a]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Imidazo[1,2-a]pyridine is a heterocyclic compound with notable applications in medicinal chemistry, particularly as a scaffold for developing kinase inhibitors targeting c-Met and VEGFR2, which exhibit potent antitumor activity. It can also be synthesized efficiently through various methods, including reactions involving 2-aminopyridines and bromohydroxycycloalkyl ethanones or dimethylketal tosylates under mild conditions, yielding electron-deficient derivatives. These synthetic approaches highlight its versatility as a pharmacophore and its potential in drug discovery.

Technology Process of Imidazo[1,2-a]pyridine

There total 33 articles about Imidazo[1,2-a]pyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-aminopyridine (504-29-0) + 2-chloroethanal (107-20-0) → imidazo[1,2-a]pyridine (274-76-0)

Guidance literature:

at 70 ℃;

DOI:10.1021/acs.jmedchem.0c02064

Reference yield: 99.0%

imidazo[1,2-a]pyridine-3-carboxylic acid (6200-60-8) → imidazo[1,2-a]pyridine (274-76-0)

Guidance literature:

With C₄₆H₄₈N₆O₅Pd; potassium acetate; In N,N-dimethyl acetamide; at 160 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jo3015837

Reference yield: 83.0%

3-bromoimidazo[1,2-a]pyridine (4926-47-0) → imidazo[1,2-a]pyridine (274-76-0)

Guidance literature:

With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; palladium diacetate; triphenylphosphine; In tetrahydrofuran; at 25 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.molcata.2014.06.012

upstream raw materials:

2-aminopyridine

1-bromo-2,2-dimethoxyethane

bromoacetaldehyde

2-chloroethanal

Downstream raw materials:

imidazo[1,2-a]pyridine-3-carbaldehyde

N-methylimidazo[1,2-a]pyridinium iodide

3-hydroxymethylimidazo[1,2-a]pyridine

3-(1-Hydroxyethyl)imidazo<1,2-a>pyridine

Refernces

Structure-based design, synthesis, and evaluation of imidazo[1,2-b] pyridazine and imidazo[1,2-a]pyridine derivatives as novel dual c-Met and VEGFR2 kinase inhibitors

10.1016/j.bmc.2013.10.028

This research endeavored to develop novel dual c-Met and VEGFR2 kinase inhibitors with potent antitumor efficacy against various human cancers. The study aimed to synthesize compounds that could inhibit both the c-mesenchymal epithelial transition factor (c-Met) and vascular endothelial growth factor receptor 2 (VEGFR2) kinases, which play significant roles in tumor growth, invasion, metastasis, and angiogenesis. Through structure-based design and synthesis, the researchers identified imidazo[1,2-b]pyridazine and imidazo[1,2-a]pyridine derivatives, with particular emphasis on compound 26, an imidazo[1,2-a]pyridine derivative bearing a 6-methylpyridone ring. This compound strongly inhibited both c-Met and VEGFR2 enzyme activities, as well as the proliferation of c-Met-addicted MKN45 cells and VEGF-stimulated human umbilical vein endothelial cells (HUVEC), demonstrating dose-dependent antitumor efficacy in vivo in mouse xenograft models. The research concluded that compound 26 has promising therapeutic potential for the treatment of human cancers.

Synthesis of Imidazo[1,2-a]pyridines and Imidazo[2,1-b]thiazoles Attached to a Cycloalkyl or Saturated Heterocycle Containing a Tertiary Hydroxy Substitution

10.1002/jhet.3454

The research focuses on the synthesis of imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles with tertiary hydroxy substitutions, utilizing readily available substituted 2-aminopyridines, 2-aminothiazoles, and 2-aminobenzothiazoles. The experiments involved treating these amines with bromohydroxycycloalkyl ethanones under various reaction conditions to optimize yields, with sodium bicarbonate as the base in 1,4-dioxane at elevated temperatures yielding the best results. The reactants included substituted acylbromides and different amino compounds, while the analyses employed included NMR spectroscopy for structural confirmation and high-resolution mass spectrometry for molecular weight determination. The study successfully demonstrated a more efficient synthetic route for these compounds, filling gaps in existing literature on related structures.

General Method for the Preparation of Electron-Deficient Imidazo[1,2-a]pyridines and Related Heterocycles

10.1021/acs.orglett.5b02966

The study presents a novel annulation method for synthesizing electron-deficient imidazo[1,2-a]pyridines and related heterocycles under mild conditions. The process involves treating 2-aminopyridines with a dimethylketal tosylate in acetonitrile at elevated temperatures (80?140 °C) in the presence of catalytic Sc(OTf)3, yielding the desired imidazo[1,2-a]pyridine products in good yields. This method is particularly useful for electron-poor 2-aminopyridines and offers an alternative to the traditional synthesis involving bromoketones with electron-rich and -neutral substrates. The study explores the scope and mechanism of the reaction, discussing the role of various additives and solvents in the cyclization process. The chemicals used in the study include 2-aminopyridines, dimethylketals (specifically tosyl ketal 3), and the catalyst Sc(OTf)3, which serve to facilitate the formation of the imidazo[1,2-a]pyridine ring system through an imine intermediate pathway.