3-[3-Bromo-2-(2-trifluoromethanesulfonylamino-phenyl)-benzofuran-5-ylmethyl]-5-chloro-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester

Base Information

• Chemical Name: 3-[3-Bromo-2-(2-trifluoromethanesulfonylamino-phenyl)-benzofuran-5-ylmethyl]-5-chloro-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester
• CAS No.: 145824-24-4
• Molecular Formula: C₂₅H₂₂BrClF₃N₃O₅S
• Molecular Weight: 648.885
• Mol file: 145824-24-4.mol

Synonyms:3-[3-Bromo-2-(2-trifluoromethanesulfonylamino-phenyl)-benzofuran-5-ylmethyl]-5-chloro-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester

Chemical Property of 3-[3-Bromo-2-(2-trifluoromethanesulfonylamino-phenyl)-benzofuran-5-ylmethyl]-5-chloro-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[3-Bromo-2-(2-trifluoromethanesulfonylamino-phenyl)-benzofuran-5-ylmethyl]-5-chloro-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester

There total 14 articles about 3-[3-Bromo-2-(2-trifluoromethanesulfonylamino-phenyl)-benzofuran-5-ylmethyl]-5-chloro-2-propyl-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:

trifluoromethylsulfonic anhydride (358-23-6) + ethyl 1-[[2-(2-aminophenyl)-3-bromo-5-benzofuranyl]methyl]-4-chloro-2-propyl-1H-imidazole-5-carboxylate (145824-23-3) → 3-[3-Bromo-2-(2-trifluoromethanesulfonylamino-phenyl)-benzofuran-5-ylmethyl]-5-chloro-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester (145824-24-4)

Guidance literature:

With triethylamine; In dichloromethane; at -70 ℃; for 0.75h;

DOI:10.1021/jm00045a016

Reference yield:

5-methylbenzofuran (18441-43-5) → 3-[3-Bromo-2-(2-trifluoromethanesulfonylamino-phenyl)-benzofuran-5-ylmethyl]-5-chloro-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester (145824-24-4)

Guidance literature:

Multi-step reaction with 10 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: 63 percent / K₂CO₃ / dimethylformamide / 20 h / Ambient temperature

7: 91 percent / 2-methyl-2-butene, sodium hypochlorite, sodium dihydrogen phosphate dihydrate / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 20 h / Ambient temperature

8: 88 percent / DEAD, triphenylphosphine / tetrahydrofuran / 20 h / Ambient temperature

9: trifluoroacetic acid / CH₂Cl₂ / 16 h / Ambient temperature

10: Et₃N / CH₂Cl₂ / 0.75 h / -70 °C

With sodium hydroxide; sodium hypochlorite; sodium dihydrogenphosphate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; Perbenzoic acid; 2-methyl-but-2-ene; Triisopropyl borate; N,N,N,N,-tetramethylethylenediamine; diphenyl phosphoryl azide; bromine; sodium carbonate; potassium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jm00045a016

Reference yield:

2-bromobenzoic acid methyl ester (610-94-6) → 3-[3-Bromo-2-(2-trifluoromethanesulfonylamino-phenyl)-benzofuran-5-ylmethyl]-5-chloro-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester (145824-24-4)

Guidance literature:

Multi-step reaction with 10 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: 63 percent / K₂CO₃ / dimethylformamide / 20 h / Ambient temperature

7: 91 percent / 2-methyl-2-butene, sodium hypochlorite, sodium dihydrogen phosphate dihydrate / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 20 h / Ambient temperature

8: 88 percent / DEAD, triphenylphosphine / tetrahydrofuran / 20 h / Ambient temperature

9: trifluoroacetic acid / CH₂Cl₂ / 16 h / Ambient temperature

10: Et₃N / CH₂Cl₂ / 0.75 h / -70 °C

With sodium hydroxide; sodium hypochlorite; sodium dihydrogenphosphate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; Perbenzoic acid; 2-methyl-but-2-ene; Triisopropyl borate; N,N,N,N,-tetramethylethylenediamine; diphenyl phosphoryl azide; bromine; sodium carbonate; potassium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jm00045a016

upstream raw materials:

trifluoromethylsulfonic anhydride

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

5-methylbenzofuran

2-bromobenzoic acid methyl ester

Downstream raw materials:

3-[3-Bromo-2-(2-trifluoromethanesulfonylamino-phenyl)-benzofuran-5-ylmethyl]-5-chloro-2-propyl-3H-imidazole-4-carboxylic acid