Ethyl 1-[[3-bromo-2-(2-aminophenyl)-5-benzofuranyl]methyl]-2,4-dimethyl-1H-imidazole-5-carboxylate

Base Information

• Chemical Name: Ethyl 1-[[3-bromo-2-(2-aminophenyl)-5-benzofuranyl]methyl]-2,4-dimethyl-1H-imidazole-5-carboxylate
• CAS No.: 1027957-17-0
• Molecular Formula: C₂₃H₂₂BrN₃O₃
• Molecular Weight: 468.35

Synonyms:Ethyl 1-[[3-bromo-2-(2-aminophenyl)-5-benzofuranyl]methyl]-2,4-dimethyl-1H-imidazole-5-carboxylate

Chemical Property of Ethyl 1-[[3-bromo-2-(2-aminophenyl)-5-benzofuranyl]methyl]-2,4-dimethyl-1H-imidazole-5-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of Ethyl 1-[[3-bromo-2-(2-aminophenyl)-5-benzofuranyl]methyl]-2,4-dimethyl-1H-imidazole-5-carboxylate

There total 10 articles about Ethyl 1-[[3-bromo-2-(2-aminophenyl)-5-benzofuranyl]methyl]-2,4-dimethyl-1H-imidazole-5-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:

3-[3-Bromo-2-(2-tert-butoxycarbonylamino-phenyl)-benzofuran-5-ylmethyl]-2,5-dimethyl-3H-imidazole-4-carboxylic acid ethyl ester (1026856-18-7) → Ethyl 1-[[3-bromo-2-(2-aminophenyl)-5-benzofuranyl]methyl]-2,4-dimethyl-1H-imidazole-5-carboxylate (1027957-17-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1021/jm00045a016

Reference yield:

5-methylbenzofuran (18441-43-5) → Ethyl 1-[[3-bromo-2-(2-aminophenyl)-5-benzofuranyl]methyl]-2,4-dimethyl-1H-imidazole-5-carboxylate (1027957-17-0)

Guidance literature:

Multi-step reaction with 7 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 / 16 h / Ambient temperature

7: trifluoroacetic acid / CH₂Cl₂ / 16 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; trifluoroacetic acid; In 1,4-dioxane; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00045a016

Reference yield:

2-bromobenzoic acid methyl ester (610-94-6) → Ethyl 1-[[3-bromo-2-(2-aminophenyl)-5-benzofuranyl]methyl]-2,4-dimethyl-1H-imidazole-5-carboxylate (1027957-17-0)

Guidance literature:

Multi-step reaction with 7 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 / 16 h / Ambient temperature

7: trifluoroacetic acid / CH₂Cl₂ / 16 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; trifluoroacetic acid; In 1,4-dioxane; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00045a016

upstream raw materials:

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

5-methylbenzofuran

2-bromobenzoic acid methyl ester

2-(3-bromo-5-methyl-2-benzofuranyl)benzoic acid

Downstream raw materials:

Ethyl 1-[[3-bromo-2-[2-[[(trifluoromethyl)sulphonyl]amino]phenyl]-5-benzofuranyl]methyl]-2,4-dimethyl-1H-imidazole-5-carboxylate

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

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