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

Base Information

• Chemical Name: ethyl 5-cyclopropyl-2-(4-fluorophenyl)-6-nitrobenzofuran-3-carboxylate
• CAS No.: 691857-52-0
• Molecular Formula: C₂₀H₁₆FNO₅
• Molecular Weight: 369.349
• Mol file: 691857-52-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about ethyl 5-cyclopropyl-2-(4-fluorophenyl)-6-nitrobenzofuran-3-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: 86.0%

ethyl 2-(4-fluorophenyl)-6-nitro-5-(trifluoromethylsulfonyloxy)benzofuran-3-carboxylate (691857-51-9) + cyclopropylboronic acid (411235-57-9) → ethyl 5-cyclopropyl-2-(4-fluorophenyl)-6-nitrobenzofuran-3-carboxylate (691857-52-0)

Guidance literature:

With potassium fluoride; sodium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; Heating / reflux;

Reference yield: 86.0%

ethyl 5-bromo-2-(4-fluorophenyl)-6-nitrobenzofuran-3-carboxylate (1333340-14-9) + cyclopropylboronic acid (411235-57-9) → ethyl 5-cyclopropyl-2-(4-fluorophenyl)-6-nitrobenzofuran-3-carboxylate (691857-52-0)

Guidance literature:

With palladium diacetate; potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether; In water; toluene; at 70 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.joc.5b01598

Reference yield:

ethyl 3-(4'-fluorophenyl)-3-oxopropionate (1999-00-4) → ethyl 5-cyclopropyl-2-(4-fluorophenyl)-6-nitrobenzofuran-3-carboxylate (691857-52-0)

Guidance literature:

Multi-step reaction with 3 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

With copper(l) iodide; palladium diacetate; potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether; In water; N,N-dimethyl-formamide; toluene; 3: |Suzuki Coupling;

DOI:10.1021/acs.joc.5b01598

upstream raw materials:

ethyl 2-(4-fluorophenyl)-6-nitro-5-(trifluoromethylsulfonyloxy)benzofuran-3-carboxylate

cyclopropylboronic acid

1-(4-fluorophenyl)ethanone

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

Downstream raw materials:

ethyl 6-amino-5-cyclopropyl-2-(4-fluorophenyl)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

N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl]-N-[2-(ethylsulfonyl)ethyl]methanesulfonamide