methyl 5-((N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(4-(trifluoromethyl)phenyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-iodobenzoate

Base Information

• Chemical Name: methyl 5-((N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(4-(trifluoromethyl)phenyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-iodobenzoate
• CAS No.: 1378430-79-5
• Molecular Formula: C₃₀H₂₆F₃IN₂O₆S
• Molecular Weight: 726.512

Synonyms:methyl 5-((N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(4-(trifluoromethyl)phenyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-iodobenzoate

Chemical Property of methyl 5-((N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(4-(trifluoromethyl)phenyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-iodobenzoate

Chemical Property:

Purity/Quality:

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Technology Process of methyl 5-((N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(4-(trifluoromethyl)phenyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-iodobenzoate

There total 12 articles about methyl 5-((N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(4-(trifluoromethyl)phenyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-iodobenzoate 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: 87.0%

2-(4-chlorophenyl)-5-cyclopropyl-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (1331943-24-8) + 5-(bromomethyl)-2-iodobenzoic acid methyl ester (125735-34-4) → methyl 5-((N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(4-(trifluoromethyl)phenyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-iodobenzoate (1378430-79-5)

Guidance literature:

With potassium carbonate; In acetonitrile; at 70 ℃; Inert atmosphere;

Reference yield:

p-benzoquinone (106-51-4) → methyl 5-((N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(4-(trifluoromethyl)phenyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-iodobenzoate (1378430-79-5)

Guidance literature:

Multi-step reaction with 11 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

8.1: triethylamine / dichloromethane / 2 h / -15 - 20 °C

9.1: potassium hydroxide; water / ethanol / 1 h / Reflux; Inert atmosphere

10.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 20 °C

10.2: 2 h

11.1: potassium carbonate / acetonitrile / 70 °C / Inert atmosphere

With dmap; potassium fluoride; [({2-[{5-cyclopropyl-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}(methylsulfonyl)amino]ethyl}oxy)methyl]boronic acid; water; hydrogen; nitric acid; boron trichloride; potassium carbonate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium bromide; potassium hydroxide; 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; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

ethyl (4-chlorobenzoyl)acetate (2881-63-2) → methyl 5-((N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(4-(trifluoromethyl)phenyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-iodobenzoate (1378430-79-5)

Guidance literature:

Multi-step reaction with 11 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

8.1: triethylamine / dichloromethane / 2 h / -15 - 20 °C

9.1: potassium hydroxide; water / ethanol / 1 h / Reflux; Inert atmosphere

10.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 20 °C

10.2: 2 h

11.1: potassium carbonate / acetonitrile / 70 °C / Inert atmosphere

With dmap; potassium fluoride; [({2-[{5-cyclopropyl-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}(methylsulfonyl)amino]ethyl}oxy)methyl]boronic acid; water; hydrogen; nitric acid; boron trichloride; potassium carbonate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium bromide; potassium hydroxide; 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; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

p-benzoquinone

ethyl (4-chlorobenzoyl)acetate

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

5-(bromomethyl)-2-iodobenzoic acid methyl ester

Downstream raw materials:

methyl 5-((N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(4-(trifluoromethyl)phenyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

5-cyclopropyl-6-(N-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)methylsulfonamido)-N-methyl-2-(4-(trifluoromethyl)phenyl)benzofuran-3-carboxamide

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