Methyl imidazo[1,5-a]pyridine-6-carboxylate

Base Information

• Chemical Name: Methyl imidazo[1,5-a]pyridine-6-carboxylate
• CAS No.: 139183-89-4
• Molecular Formula: C9H8N2O2
• Molecular Weight: 176.175
• Hs Code.: 2933990090
• European Community (EC) Number: 831-807-3
• DSSTox Substance ID: DTXSID50440997
• Wikidata: Q82257524
• Mol file: 139183-89-4.mol

Synonyms:Methyl imidazo[1,5-a]pyridine-6-carboxylate;139183-89-4;Imidazo[1,5-a]pyridine-6-carboxylic acid, methyl ester;methylimidazo[1,5-a]pyridine-6-carboxylate;SCHEMBL322086;DTXSID50440997;MUBQQJSSJDOSKH-UHFFFAOYSA-N;MFCD23102989;AS-69530;CS-0196758;FT-0750206;D70694;EN300-125610;Imidazo[1,5-a]pyridine-6-carboxylic acid methyl ester

Chemical Property of Methyl imidazo[1,5-a]pyridine-6-carboxylate

Chemical Property:

• PSA: 43.60000
• LogP: 1.12090
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 176.058577502
• Heavy Atom Count: 13
• Complexity: 208

Purity/Quality:

98%min ^*data from raw suppliers

Methylimidazo[1,5-a]pyridine-6-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CN2C=NC=C2C=C1

Technology Process of Methyl imidazo[1,5-a]pyridine-6-carboxylate

There total 4 articles about Methyl imidazo[1,5-a]pyridine-6-carboxylate 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: 94.0%

methyl 6-formylaminomethylnicotinate (139183-88-3) → methyl imidazo[1,5-a] pyridine-6-carboxylate (139183-89-4)

Guidance literature:

With trichlorophosphate; In dichloromethane; for 1h; Heating;

DOI:10.1248/cpb.44.991

Reference yield: 71.0%

→ methyl imidazo[1,5-a] pyridine-6-carboxylate (139183-89-4)

Guidance literature:

Reference yield:

methyl 6-hydroxyiminomethylnicotinate (22794-96-3) → methyl imidazo[1,5-a] pyridine-6-carboxylate (139183-89-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / Zn, aq. AcOH

2: 60 percent / Heating

3: 94 percent / POCl₃ / CH₂Cl₂ / 1 h / Heating

With acetic acid; zinc; trichlorophosphate; In dichloromethane;

DOI:10.1248/cpb.44.991

upstream raw materials:

methyl 6-formylaminomethylnicotinate

methyl 6-hydroxyiminomethylnicotinate

methyl 6-(aminomethyl)nicotinate

Downstream raw materials:

methyl 3-{[3-(methoxycarbonyl)-4-[(propylcarbamoyl)amino]phenyl]carbonyl}imidazo[1,5-a]pyridine-6-carboxylate

3-[(4-amino-3-carboxyphenyl)carbonyl]imidazo[1,5-a]pyridine-6-carboxylic acid

N-{[4-(benzenesulfonyl)phenyl]methyl}imidazo[1,5-a]pyridine-6-carboxamide

imidazo[1,5-a]pyridine-6-carboxylic acid

Refernces

• 1、 Li, Qun,Woods, Keith W.,Claiborne, Akiyo,Gwaltney, Ii, Stephen L.,Barr, Kenneth J.,Liu, Gang,Gehrke, Laura,Credo,Hui, Yu Hua,Lee, Jang,Warner, Robert B.,Kovar, Peter,Nukkala, Michael A.,Zielinski, Nicolette A.,Tahir, Stephen K.,Fitzgerald, Michael,Kim, Ki H.,Marsh, Kennan,Frost, David,Ng, Shi-Chung,Rosenberg, Saul,Sham, Hing L.. "Synthesis and biological evaluation of 2-Indolyloxazolines as a new class of tubulin polymerization inhibitors. Discovery of A-289099 as an orally active antitumor agent". . p. 465 - 469. Retrieved 2007/10/03.
• 2、 -. "TETRAHYDROIMIDAZOPYRIDINE DERIVATIVES AND SALTS THEREOF". . . Retrieved 2008/06/13.