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

Base Information

• Chemical Name: 3-[3-Bromo-2-(2-tert-butoxycarbonylamino-phenyl)-benzofuran-5-ylmethyl]-2,5-diethyl-3H-imidazole-4-carboxylic acid ethyl ester
• CAS No.: 146650-67-1
• Molecular Formula: C₃₀H₃₄BrN₃O₅
• Molecular Weight: 596.521

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

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

Chemical Property:

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

There total 10 articles about 3-[3-Bromo-2-(2-tert-butoxycarbonylamino-phenyl)-benzofuran-5-ylmethyl]-2,5-diethyl-3H-imidazole-4-carboxylic acid ethyl ester 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:

2-Nitro-3-oxo-pentanoic acid ethyl ester → 3-[3-Bromo-2-(2-tert-butoxycarbonylamino-phenyl)-benzofuran-5-ylmethyl]-2,5-diethyl-3H-imidazole-4-carboxylic acid ethyl ester (146650-67-1)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂, AcCl / 5percent Pd/C / ethanol / 5 h / 760 Torr / Ambient temperature

2: Et₃N / ethanol

3: K₂CO₃ / dimethylformamide / 16 h / Ambient temperature

With hydrogen; potassium carbonate; triethylamine; acetyl chloride; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00045a016

Reference yield:

ethyl propanoylacetate (4949-44-4) → 3-[3-Bromo-2-(2-tert-butoxycarbonylamino-phenyl)-benzofuran-5-ylmethyl]-2,5-diethyl-3H-imidazole-4-carboxylic acid ethyl ester (146650-67-1)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. NaNO₂ / acetic acid / 4 h / Ambient temperature

2: H₂, AcCl / 5percent Pd/C / ethanol / 5 h / 760 Torr / Ambient temperature

3: Et₃N / ethanol

4: K₂CO₃ / dimethylformamide / 16 h / Ambient temperature

With hydrogen; potassium carbonate; triethylamine; acetyl chloride; sodium nitrite; palladium on activated charcoal; In ethanol; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jm00045a016

Reference yield:

5-methylbenzofuran (18441-43-5) → 3-[3-Bromo-2-(2-tert-butoxycarbonylamino-phenyl)-benzofuran-5-ylmethyl]-2,5-diethyl-3H-imidazole-4-carboxylic acid ethyl ester (146650-67-1)

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 / 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; In 1,4-dioxane; methanol; tetrachloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00045a016

upstream raw materials:

2,5-Diethyl-3H-imidazole-4-carboxylic acid ethyl ester

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

5-methylbenzofuran

2-bromobenzoic acid methyl ester

Downstream raw materials:

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

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

3-[2-(2-Amino-phenyl)-3-bromo-benzofuran-5-ylmethyl]-2,5-diethyl-3H-imidazole-4-carboxylic acid ethyl ester

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