(6-METHYL-2-P-TOLYL-IMIDAZO[1,2-A]PYRIDIN-3-YL)-ACETONITRILE

Base Information

• Chemical Name: (6-METHYL-2-P-TOLYL-IMIDAZO[1,2-A]PYRIDIN-3-YL)-ACETONITRILE
• CAS No.: 768398-03-4
• Molecular Formula: C17H15 N3
• Molecular Weight: 261.326
• Hs Code.: 2933990090
• Mol file: 768398-03-4.mol

Synonyms:Zolpidem IV

Chemical Property of (6-METHYL-2-P-TOLYL-IMIDAZO[1,2-A]PYRIDIN-3-YL)-ACETONITRILE

Chemical Property:

• Refractive Index: 1.625
• PKA: 5.86±0.50(Predicted)
• PSA: 41.09000
• Density: 1.12g/cm³
• LogP: 3.68418
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

2-(6-Methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)acetonitrile 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Impurity of Zolpidem (Z650000), a selective non-benzodiazepine GABAA receptor agonist.

Technology Process of (6-METHYL-2-P-TOLYL-IMIDAZO[1,2-A]PYRIDIN-3-YL)-ACETONITRILE

There total 12 articles about (6-METHYL-2-P-TOLYL-IMIDAZO[1,2-A]PYRIDIN-3-YL)-ACETONITRILE 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: 85.0%

6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyridine (88965-00-8) + cyanomethyl bromide (590-17-0) → 6-methyl-3-cyanomethyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine (768398-03-4)

Guidance literature:

With fac-tris(2-phenylpyridinato-N,C₂')iridium(III); sodium hydrogencarbonate; In dimethyl sulfoxide; at 20 ℃; for 12h; regioselective reaction; Schlenk technique; Inert atmosphere; Irradiation;

DOI:10.1021/acs.joc.7b00750

Reference yield: 85.0%

→ 6-methyl-3-cyanomethyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine (768398-03-4)

Guidance literature:

With tris[2-phenylpyridinato-C²,N]iridium(III); sodium hydrogencarbonate; In dimethyl sulfoxide; at 20 ℃; for 12h; Inert atmosphere; Microwave irradiation;

Reference yield: 61.0%

S-cyanomethyl O-ethyl carbonodithioate (59463-54-6) + 6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyridine (88965-00-8) → 6-methyl-3-cyanomethyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine (768398-03-4)

Guidance literature:

With tris[2-phenylpyridinato-C₂,N]iridium(III); N,N-dimethyl-formamide; at 24 ℃; regioselective reaction; Inert atmosphere; UV-irradiation;

DOI:10.1016/j.tet.2018.04.079

upstream raw materials:

sodium cyanide

Trimethyl-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-ylmethyl)-ammonium; iodide

potassium cyanide

dimethyl-(6-methyl-2-p-tolylimidazo[1,2-a]pyridin-3-ylmethyl)-amine

Downstream raw materials:

ethyl 6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine-3-acetate

N,N,6-trimethyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine-3-acetamide

3-((2H-tetrazol-5-yl)methyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine

6-methyl-2-(4-methylphenyl)-imidazo<1,2-a>pyridine-3-acetic acid

Refernces

• 1、 -. "A cyanogen methylation imidazopyridine compound of preparation method (by machine translation)". Paragraph 0026; 0069; 0070. . Retrieved 2019/03/02.
• 2、 Pérez, Víctor M.,Fregoso-López, Daniela,Miranda, Luis D.. "Xanthate-based microwave-assisted C–H radical functionalization of caffeine, 1,3-dimethyluracil, and imidazo[1,2-a]pyridines". supporting information. p. 1326 - 1329. Retrieved 2017/03/10.