tert-Butyl 2-oxo-1H-imidazo[4,5-b]pyridine-3(2H)-carboxylate

Base Information

• Chemical Name: tert-Butyl 2-oxo-1H-imidazo[4,5-b]pyridine-3(2H)-carboxylate
• CAS No.: 1027159-01-8
• Molecular Formula: C11H13N3O3
• Molecular Weight: 235.23900
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID80433812
• Mol file: 1027159-01-8.mol

Synonyms:1027159-01-8;tert-Butyl 2-oxo-1H-imidazo[4,5-b]pyridine-3(2H)-carboxylate;tert-butyl 2-oxo-1H-imidazo[4,5-b]pyridine-3-carboxylate;3H-Imidazo[4,5-b]pyridine-3-carboxylic acid, 1,2-dihydro-2-oxo-, 1,1-dimethylethyl ester;DTXSID80433812;tert-Butyl2-oxo-1H-imidazo[4,5-b]pyridine-3(2H)-carboxylate;CS-0444821;F18722;A896721;Tert-butyl 2-hydroxy-3H-imidazo[4,5-b]pyridine-3-carboxylate;tert-Butyl 2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridine-3-carboxylate;1,2-Dihydro-2-oxo-3H-imidazo[4,5-b]pyridine-3-carboxylic acid,1,1-dimethyl ethyl ester

Chemical Property of tert-Butyl 2-oxo-1H-imidazo[4,5-b]pyridine-3(2H)-carboxylate

Chemical Property:

• PSA: 77.24000
• LogP: 1.92010
• Storage Temp.: 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 235.09569129
• Heavy Atom Count: 17
• Complexity: 337

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl2-oxo-1H-imidazo[4,5-b]pyridine-3(2H)-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C2=C(C=CC=N2)NC1=O

Technology Process of tert-Butyl 2-oxo-1H-imidazo[4,5-b]pyridine-3(2H)-carboxylate

There total 6 articles about tert-Butyl 2-oxo-1H-imidazo[4,5-b]pyridine-3(2H)-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: 76.0%

di-tert-butyl dicarbonate (24424-99-5) + 2,3-Dihydro-2-oxo-1H-imidazo<4,5-b>pyridine-1-carboxylic acid ethyl ester (103409-28-5) → 1,2-Dihydro-2-oxo-3H-imidazo<4,5-b>pyridine-3-carboxylic acid 1,1-dimethylethyl ester (1027159-01-8)

Guidance literature:

di-tert-butyl dicarbonate; 2,3-Dihydro-2-oxo-1H-imidazo<4,5-b>pyridine-1-carboxylic acid ethyl ester; With dmap; In tetrahydrofuran; for 2h; Reflux; Inert atmosphere;

With isopropylamine; In tetrahydrofuran; for 0.75h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b00874

Reference yield:

1,3-dihydro-imidazo[4,5-b]pyridin-2-one (16328-62-4) → 1,2-Dihydro-2-oxo-3H-imidazo<4,5-b>pyridine-3-carboxylic acid 1,1-dimethylethyl ester (1027159-01-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / K₂CO₃ / acetonitrile / 1.5 h / Heating

2: DMAP / tetrahydrofuran / 1 h

3: i-PrNH₂ / tetrahydrofuran / 0.33 h

With dmap; potassium carbonate; isopropylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo00111a014

Reference yield:

2-Oxo-imidazo[4,5-b]pyridine-1,3-dicarboxylic acid 3-tert-butyl ester 1-ethyl ester → 1,2-Dihydro-2-oxo-3H-imidazo<4,5-b>pyridine-3-carboxylic acid 1,1-dimethylethyl ester (1027159-01-8)

Guidance literature:

With isopropylamine; In tetrahydrofuran; for 0.333333h; Yield given;

DOI:10.1021/jo00111a014

upstream raw materials:

1,3-dihydro-imidazo[4,5-b]pyridin-2-one

2,3-Dihydro-2-oxo-1H-imidazo<4,5-b>pyridine-1-carboxylic acid ethyl ester

di-tert-butyl dicarbonate

2,3-Diaminopyridine

Downstream raw materials:

1-Cyclohexylmethyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridine-3-carboxylic acid tert-butyl ester

1-Benzyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridine-3-carboxylic acid tert-butyl ester