3-Benzofurancarboxylic acid, 6-aMino-5-cyclopropyl-2-(4-fluorophenyl)-, ethyl ester

Base Information

• Chemical Name: 3-Benzofurancarboxylic acid, 6-aMino-5-cyclopropyl-2-(4-fluorophenyl)-, ethyl ester
• CAS No.: 691857-53-1
• Molecular Formula: C20H18FNO3
• Molecular Weight: 339.366
• Mol file: 691857-53-1.mol

Synonyms:3-Benzofurancarboxylic acid, 6-aMino-5-cyclopropyl-2-(4-fluorophenyl)-, ethyl ester;ethyl6-amino-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylate

Chemical Property of 3-Benzofurancarboxylic acid, 6-aMino-5-cyclopropyl-2-(4-fluorophenyl)-, ethyl ester

Chemical Property:

• PSA: 65.46000
• LogP: 5.45640

Purity/Quality:

NLT 98% ^*data from raw suppliers

3-Benzofurancarboxylicacid,6-amino-5-cyclopropyl-2-(4-fluorophenyl)-,ethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Benzofurancarboxylic acid, 6-aMino-5-cyclopropyl-2-(4-fluorophenyl)-, ethyl ester

There total 11 articles about 3-Benzofurancarboxylic acid, 6-aMino-5-cyclopropyl-2-(4-fluorophenyl)-, 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: 88.0%

ethyl 5-cyclopropyl-2-(4-fluorophenyl)-6-nitrobenzofuran-3-carboxylate (691857-52-0) → ethyl 6-amino-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylate (691857-53-1)

Guidance literature:

With hydrogenchloride; hydrogen; palladium 10% on activated carbon; In water; ethyl acetate; under 3345.86 Torr;

Reference yield:

ethyl 3-(4'-fluorophenyl)-3-oxopropionate (1999-00-4) → ethyl 6-amino-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylate (691857-53-1)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / N,N-dimethyl-formamide / 20 h / 20 - 45 °C / Inert atmosphere

2: copper(l) iodide / N,N-dimethyl-formamide / 20 h / 60 °C / Inert atmosphere

3: potassium carbonate; palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether / toluene; water / 2 h / 70 °C / Inert atmosphere

4: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 15 h / 30 °C / 15 Torr / Inert atmosphere

With copper(l) iodide; palladium 10% on activated carbon; hydrogen; palladium diacetate; potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 3: |Suzuki Coupling;

DOI:10.1021/acs.joc.5b01598

Reference yield:

ethyl 2-(4-fluorophenyl)-5-hydroxy-6-nitrobenzofuran-3-carboxylate (691857-46-2) → ethyl 6-amino-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylate (691857-53-1)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide; acetonitrile / 2 h / 0 °C

2: sodium bromide; potassium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 16 h / 110 °C

3: zinc; ammonium chloride / tetrahydrofuran; methanol; water / 6 h / 80 °C

With dmap; potassium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium chloride; N-ethyl-N,N-diisopropylamine; sodium bromide; zinc; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

ethyl 5-cyclopropyl-2-(4-fluorophenyl)-6-nitrobenzofuran-3-carboxylate

1-(4-fluorophenyl)ethanone

ethyl 3-(4'-fluorophenyl)-3-oxopropionate

ethyl 2-(4-fluorophenyl)-5-hydroxy-6-nitrobenzofuran-3-carboxylate

Downstream raw materials:

C₂₀H₁₈FNO₇S₂

ethyl 5-cyclopropyl-2-(4-fluorophenyl)-6-[(methylsulfonyl)amino]-1-benzofuran-3-carboxylate

4-{[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl](methylsulfonyl)amino}butanoic acid

5-{[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl](methylsulfonyl)amino}pentanamide