1,6-Dimethyl-1H-imidazo[4,5-b]pyridine

Base Information

• Chemical Name: 1,6-Dimethyl-1H-imidazo[4,5-b]pyridine
• CAS No.: 147057-13-4
• Molecular Formula: C₈H₉N₃
• Molecular Weight: 147.18
• DSSTox Substance ID: DTXSID901282270
• Nikkaji Number: J702.074K
• Mol file: 147057-13-4.mol

Synonyms:1,6-Dimethyl-1H-imidazo[4,5-b]pyridine;147057-13-4;1,6-DIMETHYLIMIDAZO[4,5-B]PYRIDINE;1H-Imidazo[4,5-b]pyridine,1,6-dimethyl-(9CI);SCHEMBL7916582;DTXSID901282270;1h-imidazo[4,5-b]pyridine,1,6-dimethyl-

Chemical Property of 1,6-Dimethyl-1H-imidazo[4,5-b]pyridine

Chemical Property:

• PSA: 30.71000
• LogP: 1.27670
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 147.079647300
• Heavy Atom Count: 11
• Complexity: 148

Purity/Quality:

1,6-dimethyl-1H-Imidazo[4,5-b]pyridine 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(N=C1)N=CN2C

Technology Process of 1,6-Dimethyl-1H-imidazo[4,5-b]pyridine

There total 6 articles about 1,6-Dimethyl-1H-imidazo[4,5-b]pyridine 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: 65.8%

1-methyl-1H-imidazol-4-amine (79578-98-6) + 2-methyl-3-phenylthioacrolein → 1,6-Dimethylimidazo<4,5-b>pyridine (147057-13-4)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; at 100 ℃; for 14h;

Reference yield: 43.7%

1,6-Dimethyl-2-(methylthio)imidazo<4,5-b>pyridin-5(4H)-one (153434-61-8) → 1,6-Dimethylimidazo<4,5-b>pyridine (147057-13-4)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; for 20h; Heating;

DOI:10.1021/jo00079a055

Reference yield:

4-Bromo-1-methyl-2-(methylthio)imidazole-5-carboxaldehyde (145083-27-8) → 1,6-Dimethylimidazo<4,5-b>pyridine (147057-13-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / tetrahydrofuran; hexane / 1.) r.t., 30 min, 2.) r.t., 12 h

2: 61.1 percent / n-BuLi / diethyl ether; hexane / 1.) -78 deg C, 1 h, 2.) r.t., 12 h

3: 99.6 percent / diphenyl phosphorazidate, Et₃N / benzene / 1 h / 50 °C

4: 75.7 percent / 1,2-dichloro-benzene / 0.25 h / 190 °C

5: 43.7 percent / NaAlH₂(OCH₂CH₂OCH₃)2 / toluene / 20 h / Heating

With n-butyllithium; diphenyl phosphoryl azide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; hexane; 1,2-dichloro-benzene; toluene; benzene;

DOI:10.1021/jo00079a055

upstream raw materials:

1,6-Dimethyl-2-(methylthio)imidazo<4,5-b>pyridin-5(4H)-one

1-methyl-1H-imidazol-4-amine

4-Bromo-1-methyl-2-(methylthio)imidazole-5-carboxaldehyde

4-Bromo-1-methyl-2-(methylthio)-5-(1-propenyl)imidazole