Production Method 1

3731-51-9

4755-77-5

81803-60-3

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  rt

Reference

Imidazopyridine CB2 agonists: Optimization of CB2/CB1 selectivity and implications for in vivo analgesic efficacy

Trotter, B. Wesley; et al, Bioorganic & Medicinal Chemistry Letters, 2011, 21(8), 2354-2358

Production Method 2

46460-25-7

81803-60-3

Reaction Conditions

1.1 Reagents: Trifluoromethanesulfonic anhydride ,  2-Methoxypyridine Solvents: 1,2-Dichloroethane ;  2 min, rt; rt → 65 °C; 24 h, 65 °C; 65 °C → rt
1.2 Reagents: Sodium bicarbonate Solvents: Water

Reference

Triflic Anhydride Mediated Synthesis of Imidazo[1,5-a]azines

Pelletier, Guillaume; et al, Organic Letters, 2013, 15(9), 2290-2293

Production Method 3

3731-51-9

4755-77-5

81803-60-3

Reaction Conditions

1.1 Solvents: Dichloromethane ;  -5 - 0 °C; 2 h, -5 - 0 °C
1.2 Reagents: Trifluoroacetic anhydride Solvents: Dichloromethane ;  -15 - -10 °C; 12 h, -15 - -10 °C

Reference

Efficient Preparation of Imidazo[1,5-a]pyridine-1-carboxylic Acids

Tverdiy, Dmytro O.; et al, Synthesis, 2016, 48(23), 4269-4277

Production Method 4

39484-31-6

81803-60-3

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  10 - 45 min, 150 - 180 °C

Reference

Microwave-assisted organic synthesis of 3-substituted-imidazo[1,5-a]pyridines

Arvapalli, Venkata Satyanarayana; et al, Tetrahedron Letters, 2010, 51(2), 284-286

Production Method 5

459-73-4

2459-07-6

81803-60-3

Reaction Conditions

1.1 Solvents: 1,4-Dioxane ;  1 h, 200 °C
2.1 Reagents: Phosphorus oxychloride ;  10 - 45 min, 150 - 180 °C

Reference

Microwave-assisted organic synthesis of 3-substituted-imidazo[1,5-a]pyridines

Arvapalli, Venkata Satyanarayana; et al, Tetrahedron Letters, 2010, 51(2), 284-286

Production Method 6

81803-59-0

81803-60-3

80537-14-0

Reaction Conditions

Reference

Vinyl azides in heterocyclic synthesis. Part 3. Isolation of azirine trimers (1,3,8-triazatricyclo[4.3.0.03,5]non-7-enes) and intramolecular interception of nitrile ylides by neighboring π-bonds or nucleophiles

Hickey, Deirdre M. B.; et al, Journal of the Chemical Society, 1986, (6), 1119-22

Production Method 7

1121-60-4

637-81-0

81803-60-3

80537-14-0

Reaction Conditions

Reference

Vinyl azides in heterocyclic synthesis. Part 3. Isolation of azirine trimers (1,3,8-triazatricyclo[4.3.0.03,5]non-7-enes) and intramolecular interception of nitrile ylides by neighboring π-bonds or nucleophiles

Hickey, Deirdre M. B.; et al, Journal of the Chemical Society, 1986, (6), 1119-22

Ethyl imidazo[1,5-a]pyridine-3-carboxylate Raw materials

• pyridine-2-carbaldehyde
• 1-(pyridin-2-yl)methanamine
• 2-Propenoic acid, 2-azido-3-(2-pyridinyl)-, ethyl ester
• Ethyl 2-Azidoacetate
• ethyl 2-chloro-2-oxo-acetate
• Glycine, ethyl ester
• Ethyl 2-(picolinamido)acetate
• Ethyl 2-oxo-2-(pyridin-2-ylmethylamino)acetate
• methyl pyridine-2-carboxylate

Ethyl imidazo[1,5-a]pyridine-3-carboxylate Preparation Products

• Ethyl pyrazolo[1,5-a]pyridine-2-carboxylate (80537-14-0)
• Ethyl imidazo[1,5-a]pyridine-3-carboxylate (81803-60-3)

• 1. Establishing new scaling relations on two-dimensional MXenes for CO2 electroreduction?
  Albertus D. Handoko,Khoong Hong Khoo,Teck Leong Tan,Hongmei Jin,Zhi Wei Seh J. Mater. Chem. A, 2018,6, 21885-21890
• 2. 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
• 3. Evolution in surface coverage of CH3NH3PbI3?XClXvia heat assisted solvent vapour treatment and their effects on photovoltaic performance of devices
  Dhirendra K. Chaudhary,Pramendra Kumar,Lokendra Kumar RSC Adv., 2016,6, 94731-94738
• 4. Fate of single walled carbon nanotubes in wetland ecosystems?
  Joseph H. Bisesi,Tara Sabo-Attwood Environ. Sci.: Nano, 2014,1, 574-583
• 5. Excitable dynamics in the bromate–sulfite–ferrocyanide reaction
  J. Zagora,M. Vosla?,L. Schreiberová,I. Schreiber Phys. Chem. Chem. Phys., 2002,4, 1284-1291

Comprehensive Overview of Ethyl imidazo[1,5-a]pyridine-3-carboxylate (CAS No. 81803-60-3)

Ethyl imidazo[1,5-a]pyridine-3-carboxylate (CAS No. 81803-60-3) is a heterocyclic organic compound that has garnered significant attention in pharmaceutical and agrochemical research due to its unique structural properties. This compound belongs to the imidazo[1,5-a]pyridine family, a class of nitrogen-containing bicyclic structures known for their versatility in drug discovery. Researchers and industry professionals frequently search for terms like "imidazo[1,5-a]pyridine derivatives", "synthesis of ethyl carboxylates", and "CAS 81803-60-3 applications", reflecting the growing interest in this molecule.

The imidazo[1,5-a]pyridine scaffold is particularly valued for its role in medicinal chemistry, where it serves as a key intermediate for developing bioactive molecules. Recent studies highlight its potential in targeting G-protein-coupled receptors (GPCRs) and kinase inhibitors, aligning with the current trend of precision medicine. With the rise of AI-driven drug discovery, compounds like Ethyl imidazo[1,5-a]pyridine-3-carboxylate are increasingly explored through computational chemistry tools, optimizing their pharmacokinetic profiles.

From a synthetic perspective, CAS 81803-60-3 is often synthesized via cyclocondensation reactions or multicomponent coupling, methods that are frequently queried in academic databases. Its ethyl ester group enhances solubility, making it a preferred choice for structure-activity relationship (SAR) studies. Environmental scientists also investigate its degradation pathways, responding to the global demand for green chemistry solutions.

In the agrochemical sector, derivatives of Ethyl imidazo[1,5-a]pyridine-3-carboxylate are explored for their pesticidal and herbicidal properties, addressing challenges like resistance management. This aligns with searches for "sustainable crop protection" and "novel agrochemical scaffolds". Regulatory agencies emphasize the need for low-toxicity alternatives, further driving research into this compound.

Analytical techniques such as HPLC, NMR, and mass spectrometry are critical for characterizing 81803-60-3, as evidenced by frequent queries about "purity analysis methods". The compound’s stability under various pH conditions is another hot topic, particularly for formulators designing drug delivery systems.

In summary, Ethyl imidazo[1,5-a]pyridine-3-carboxylate (CAS No. 81803-60-3) bridges multiple disciplines, from pharmaceutical R&D to agrochemical innovation. Its adaptability to modern high-throughput screening and computational modeling ensures its relevance in cutting-edge science. As interest in heterocyclic chemistry grows, this compound remains a focal point for researchers seeking next-generation therapeutics and eco-friendly agrochemicals.

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