Imidazo(1,2-a)pyridine-3-acetonitrile, 2-(p-chlorophenyl)-

Base Information

• Chemical Name: Imidazo(1,2-a)pyridine-3-acetonitrile, 2-(p-chlorophenyl)-
• CAS No.: 17744-99-9
• Molecular Formula: C15H10 Cl N3
• Molecular Weight: 267.717
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID10170309
• Nikkaji Number: J40.941C
• Wikidata: Q83040220
• Mol file: 17744-99-9.mol

Synonyms:17744-99-9;Imidazo(1,2-a)pyridine-3-acetonitrile, 2-(p-chlorophenyl)-;BRN 0804388;2-[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl]acetonitrile;2-(p-Chlorophenyl)-3-cyanomethylimidazo(1,2-a)pyridine;Imidazo(1,2-a)pyridine, 2-(p-chlorophenyl)-3-cyanomethyl;C15H10ClN3;2-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)acetonitrile;Imidazo[1,2-a]pyridine-3-acetonitrile, 2-(p-chlorophenyl)-;SCHEMBL1430434;DTXSID10170309;LS-80226;2-(Chlorophenyl)imidazo(1,2-a)pyridine-3-acetonile;2-(p-Chlorophenyl)imidazo[1,2-a]pyridine-3-acetonitrile;[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl]acetonitrile

Chemical Property of Imidazo(1,2-a)pyridine-3-acetonitrile, 2-(p-chlorophenyl)-

Chemical Property:

• PSA: 41.09000
• Density: 1.27g/cm³
• LogP: 3.72078
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 267.0563250
• Heavy Atom Count: 19
• Complexity: 356

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=NC(=C(N2C=C1)CC#N)C3=CC=C(C=C3)Cl

Technology Process of Imidazo(1,2-a)pyridine-3-acetonitrile, 2-(p-chlorophenyl)-

There total 8 articles about Imidazo(1,2-a)pyridine-3-acetonitrile, 2-(p-chlorophenyl)- 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: 87.0%

2-(4-chlorophenyl)imidazolo[1,2-a]pyridine (38922-74-6) + cyanomethyl bromide (590-17-0) → 2-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)acetonitrile (17744-99-9)

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: 82.0%

sodium cyanide (773837-37-9) + 3-(chloromethyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine hydrochloride → 2-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)acetonitrile (17744-99-9)

Guidance literature:

With sodium iodide; tetra-n-butylammonium cyanide; In acetonitrile; at 20 ℃;

Reference yield: 67.0%

2-(4-chlorophenyl)imidazolo[1,2-a]pyridine (38922-74-6) + acetonitrile (75-05-8,26809-02-9) → 2-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)acetonitrile (17744-99-9)

Guidance literature:

With ferrocene; bis(1-methyl-1-phenylethyl)peroxide; at 20 - 100 ℃; for 20h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.7b00678

upstream raw materials:

potassium cyanide

1-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N,N-dimethylmethanamine

2-(4-chlorophenyl)imidazolo[1,2-a]pyridine

sodium cyanide

Downstream raw materials:

C₁₉H₁₁Cl₂N₅

2-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N'-hydroxyacetimidamide

3-((2-(4-chlorophenyl)-6-fluoroimidazo[1,2-a]pyridin-3-yl)methyl)-N-hydroxy-1,2,4-oxadiazole-5-carboxamide

N₁-(6-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)pyrimidin-4-yl)-N₂,N₂-dimethylethane-1,2-diamine

Refernces

• 1、 -. "A cyanogen methylation imidazopyridine compound of preparation method (by machine translation)". Paragraph 0026; 0037; 0038. . Retrieved 2019/03/02.
• 2、 Chang, Qing,Liu, Zhengyi,Liu, Ping,Yu, Lu,Sun, Peipei. "Visible-Light-Induced Regioselective Cyanomethylation of Imidazopyridines and Its Application in Drug Synthesis". . p. 5391 - 5397. Retrieved 2017/05/24.