1H-Imidazo[4,5-b]pyridine, 1-[(4-fluorophenyl)methyl]-

Base Information

• Chemical Name: 1H-Imidazo[4,5-b]pyridine, 1-[(4-fluorophenyl)methyl]-
• CAS No.: 142872-80-8
• Molecular Formula: C13H10FN3
• Molecular Weight: 227.241
• Mol file: 142872-80-8.mol

Synonyms:

Chemical Property of 1H-Imidazo[4,5-b]pyridine, 1-[(4-fluorophenyl)methyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Imidazo[4,5-b]pyridine, 1-[(4-fluorophenyl)methyl]-

There total 3 articles about 1H-Imidazo[4,5-b]pyridine, 1-[(4-fluorophenyl)methyl]- 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: 96.0%

(2-chloropyridin-3-yl)-(4-fluorobenzyl)amine (906371-80-0) + formamide (77287-34-4,77287-35-5,60100-09-6) → 1-(4-fluorobenzyl)-1H-imidazo[4,5-b]pyridine (142872-80-8)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; potassium phosphate; In tert-butyl alcohol; at 110 ℃; for 3.5h; Schlenk technique; Inert atmosphere;

DOI:10.1039/c3ob40413g

Reference yield:

2-chloro-3-aminopyridine (6298-19-7) → 1-(4-fluorobenzyl)-1H-imidazo[4,5-b]pyridine (142872-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid; sodium tris(acetoxy)borohydride / ethyl acetate / 20 °C / Inert atmosphere

2: potassium phosphate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; t-BuBrettPhos / iso-butanol / 5 h / 110 °C / Sealed tube; Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; potassium phosphate; t-BuBrettPhos; sodium tris(acetoxy)borohydride; trifluoroacetic acid; In ethyl acetate; iso-butanol;

Reference yield:

4-fluorobenzaldehyde (459-57-4) → 1-(4-fluorobenzyl)-1H-imidazo[4,5-b]pyridine (142872-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid; sodium tris(acetoxy)borohydride / ethyl acetate / 20 °C / Inert atmosphere

2: potassium phosphate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; t-BuBrettPhos / iso-butanol / 5 h / 110 °C / Sealed tube; Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; potassium phosphate; t-BuBrettPhos; sodium tris(acetoxy)borohydride; trifluoroacetic acid; In ethyl acetate; iso-butanol;

upstream raw materials:

(2-chloropyridin-3-yl)-(4-fluorobenzyl)amine

formamide

2-chloro-3-aminopyridine

4-fluorobenzaldehyde

Downstream raw materials:

2-chloro-1-(4-fluorobenzyl)-1H-imidazo[4,5-b]pyridine

4-(1-(4-fluorobenzyl)-1H-imidazo[4,5-b]pyridin-2-yl)morpholine

Refernces

• 1、 Rosenberg, Adam J.,Ahmed, Ijaz,Wilson, Robert J.,Williams, Theresa M.,Kaminsky, Lauren,Clark, Daniel A.. "An improved synthesis of imidazo[4,5-b]pyridines and imidazo[4,5-b]pyrazines by palladium catalyzed amidation using xantphos in a 1,4-dioxane:tert-amyl alcohol solvent system". supporting information. p. 3465 - 3470. Retrieved 2015/01/09.