ethyl 6-amino-2-(4-chlorophenyl)-5-cyclopropylbenzofuran-3-carboxylate

Base Information

• Chemical Name: ethyl 6-amino-2-(4-chlorophenyl)-5-cyclopropylbenzofuran-3-carboxylate
• CAS No.: 1331943-21-5
• Molecular Formula: C₂₀H₁₈ClNO₃
• Molecular Weight: 355.821
• Mol file: 1331943-21-5.mol

Synonyms:ethyl 6-amino-2-(4-chlorophenyl)-5-cyclopropylbenzofuran-3-carboxylate

Chemical Property of ethyl 6-amino-2-(4-chlorophenyl)-5-cyclopropylbenzofuran-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 6-amino-2-(4-chlorophenyl)-5-cyclopropylbenzofuran-3-carboxylate

There total 11 articles about ethyl 6-amino-2-(4-chlorophenyl)-5-cyclopropylbenzofuran-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: 99.0%

ethyl 2-(4-chlorophenyl)-5-cyclopropyl-6-nitrobenzofuran-3-carboxylate (1331943-20-4) → ethyl 6-amino-2-(4-chlorophenyl)-5-cyclopropylbenzofuran-3-carboxylate (1331943-21-5)

Guidance literature:

With [({2-[{5-cyclopropyl-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}(methylsulfonyl)amino]ethyl}oxy)methyl]boronic acid; hydrogen; palladium 10% on activated carbon; In ethyl acetate; at 20 ℃; for 8h; under 3000.3 Torr;

Reference yield:

ethyl (4-chlorobenzoyl)acetate (2881-63-2) → ethyl 6-amino-2-(4-chlorophenyl)-5-cyclopropylbenzofuran-3-carboxylate (1331943-21-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: zinc(II) chloride / ethanol; tert-butyl methyl ether / 2 h / 75 - 95 °C / Inert atmosphere

2.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 20 h / 60 °C

3.1: nitric acid / chloroform / 2.5 h / 0 °C / Cooling with ice

4.1: boron trichloride / dichloromethane / 0.33 h / Cooling with ice; Inert atmosphere

4.2: Cooling with ice

5.1: dmap; triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

6.1: potassium fluoride; sodium bromide / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; water / 20 h / Inert atmosphere; Reflux

7.1: hydrogen; [({2-[{5-cyclopropyl-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}(methylsulfonyl)amino]ethyl}oxy)methyl]boronic acid / palladium 10% on activated carbon / ethyl acetate / 8 h / 20 °C / 3000.3 Torr

With dmap; potassium fluoride; [({2-[{5-cyclopropyl-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}(methylsulfonyl)amino]ethyl}oxy)methyl]boronic acid; hydrogen; nitric acid; boron trichloride; caesium carbonate; triethylamine; sodium bromide; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; In 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; tert-butyl methyl ether; chloroform; water; ethyl acetate; toluene;

Reference yield:

ethyl 2-(4-chlorophenyl)-5-isopropoxy-6-nitrobenzofuran-3-carboxylate (1331943-17-9) → ethyl 6-amino-2-(4-chlorophenyl)-5-cyclopropylbenzofuran-3-carboxylate (1331943-21-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: boron trichloride / dichloromethane / 0.33 h / Cooling with ice; Inert atmosphere

1.2: Cooling with ice

2.1: dmap; triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3.1: potassium fluoride; sodium bromide / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; water / 20 h / Inert atmosphere; Reflux

4.1: hydrogen; [({2-[{5-cyclopropyl-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}(methylsulfonyl)amino]ethyl}oxy)methyl]boronic acid / palladium 10% on activated carbon / ethyl acetate / 8 h / 20 °C / 3000.3 Torr

With dmap; potassium fluoride; [({2-[{5-cyclopropyl-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}(methylsulfonyl)amino]ethyl}oxy)methyl]boronic acid; hydrogen; boron trichloride; triethylamine; sodium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; In dichloromethane; water; ethyl acetate; toluene;

upstream raw materials:

p-benzoquinone

ethyl (4-chlorobenzoyl)acetate

ethyl 2-(4-chlorophenyl)-5-hydroxybenzofuran-3-carboxylate

ethyl 2-(4-chlorophenyl)-5-isopropoxybenzofuran-3-carboxylate

Downstream raw materials:

5-cyclopropyl-2-(4-chlorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylic acid

2-(4-chlorophenyl)-5-cyclopropyl-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide

6-(N-(2-(benzyloxymethyl)allyl)methylsulfonamido)-2-(4-chlorophenyl)-5-cyclopropyl-N-methylbenzofuran-3-carboxamide

6-(N-(3-(benzyloxy)-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)propyl)methylsulfonamido)-2-(4-chlorophenyl)-5-cyclopropyl-N-methylbenzofuran-3-carboxamide