1-[[3-Bromo-2-[2-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]-5-benzofuranyl]methyl]-4-chloro-2-ethyl-1H-imidazole-5-carboxaldehyde

Base Information

• Chemical Name: 1-[[3-Bromo-2-[2-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]-5-benzofuranyl]methyl]-4-chloro-2-ethyl-1H-imidazole-5-carboxaldehyde
• CAS No.: 145824-16-4
• Molecular Formula: C₂₆H₂₅BrClN₃O₄
• Molecular Weight: 558.859
• Mol file: 145824-16-4.mol

Synonyms:

Chemical Property of 1-[[3-Bromo-2-[2-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]-5-benzofuranyl]methyl]-4-chloro-2-ethyl-1H-imidazole-5-carboxaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[[3-Bromo-2-[2-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]-5-benzofuranyl]methyl]-4-chloro-2-ethyl-1H-imidazole-5-carboxaldehyde

There total 10 articles about 1-[[3-Bromo-2-[2-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]-5-benzofuranyl]methyl]-4-chloro-2-ethyl-1H-imidazole-5-carboxaldehyde 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:

5-methylbenzofuran (18441-43-5) → 1-[[3-Bromo-2-[2-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]-5-benzofuranyl]methyl]-4-chloro-2-ethyl-1H-imidazole-5-carboxaldehyde (145824-16-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi, TMEDA, 2.) triisopropyl borate, 3.) tetrakis(triphenylphosphine)palladium, Na₂CO₃

2: 100 percent / Br₂ / CCl₄ / 0.67 h / 0 - 5 °C

3: 92 percent / aq. NaOH / methanol / 3 h / Heating

4: 18 percent / diphenylphosphorazidate, Et₃N / dioxane / 20 h / Heating

5: 97 percent / NBS, benzoyl peroxide / CCl₄ / 1.5 h / Heating; Irradiation

6: K₂CO₃ / dimethylformamide / 20 h / Ambient temperature

With sodium hydroxide; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; Perbenzoic acid; Triisopropyl borate; N,N,N,N,-tetramethylethylenediamine; diphenyl phosphoryl azide; bromine; sodium carbonate; potassium carbonate; triethylamine; In 1,4-dioxane; methanol; tetrachloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00045a016

Reference yield:

2-bromobenzoic acid methyl ester (610-94-6) → 1-[[3-Bromo-2-[2-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]-5-benzofuranyl]methyl]-4-chloro-2-ethyl-1H-imidazole-5-carboxaldehyde (145824-16-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi, TMEDA, 2.) triisopropyl borate, 3.) tetrakis(triphenylphosphine)palladium, Na₂CO₃

2: 100 percent / Br₂ / CCl₄ / 0.67 h / 0 - 5 °C

3: 92 percent / aq. NaOH / methanol / 3 h / Heating

4: 18 percent / diphenylphosphorazidate, Et₃N / dioxane / 20 h / Heating

5: 97 percent / NBS, benzoyl peroxide / CCl₄ / 1.5 h / Heating; Irradiation

6: K₂CO₃ / dimethylformamide / 20 h / Ambient temperature

With sodium hydroxide; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; Perbenzoic acid; Triisopropyl borate; N,N,N,N,-tetramethylethylenediamine; diphenyl phosphoryl azide; bromine; sodium carbonate; potassium carbonate; triethylamine; In 1,4-dioxane; methanol; tetrachloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00045a016

Reference yield:

2-(3-bromo-5-methyl-2-benzofuranyl)benzoic acid (145066-95-1) → 1-[[3-Bromo-2-[2-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]-5-benzofuranyl]methyl]-4-chloro-2-ethyl-1H-imidazole-5-carboxaldehyde (145824-16-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 18 percent / diphenylphosphorazidate, Et₃N / dioxane / 20 h / Heating

2: 97 percent / NBS, benzoyl peroxide / CCl₄ / 1.5 h / Heating; Irradiation

3: K₂CO₃ / dimethylformamide / 20 h / Ambient temperature

With N-Bromosuccinimide; Perbenzoic acid; diphenyl phosphoryl azide; potassium carbonate; triethylamine; In 1,4-dioxane; tetrachloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00045a016

upstream raw materials:

4-chloro-2-ethyl-1H-imidazole-5-carboxaldehyde

1,1-dimethylethyl <2-(3-bromo-5-(bromomethyl)-2-benzofuranyl)phenyl>carbamate

5-methylbenzofuran

2-bromobenzoic acid methyl ester

Downstream raw materials:

3-[3-Bromo-2-(2-tert-butoxycarbonylamino-phenyl)-benzofuran-5-ylmethyl]-5-chloro-2-ethyl-3H-imidazole-4-carboxylic acid

ethyl 1-[[3-bromo-2-(2-aminophenyl)-5-benzofuranyl]methyl]-4-chloro-2-ethyl-1H-imidazole-5-carboxylate

1-[[3-Bromo-2-[2-[[(trifluoromethyl)sulphonyl]amino]phenyl]-5-benzofuranyl]methyl]-4-chloro-2-ethyl-1H-imidazole-5-carboxylic acid

ethyl 1-[[3-bromo-2-[2-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]-5-benzofuranyl]methyl]-4-chloro-2-ethyl-1H-imidazole-5-carboxylate