6-[N-(3-chloro-4-vinylphenyl)methanesulfonamido]-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

Base Information

• Chemical Name: 6-[N-(3-chloro-4-vinylphenyl)methanesulfonamido]-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide
• CAS No.: 1423008-17-6
• Molecular Formula: C₂₈H₂₄ClFN₂O₄S
• Molecular Weight: 539.027

Synonyms:6-[N-(3-chloro-4-vinylphenyl)methanesulfonamido]-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

Chemical Property of 6-[N-(3-chloro-4-vinylphenyl)methanesulfonamido]-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[N-(3-chloro-4-vinylphenyl)methanesulfonamido]-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

There total 15 articles about 6-[N-(3-chloro-4-vinylphenyl)methanesulfonamido]-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide 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: 90.0%

6-[N-(4-bromo-3-chlorophenyl)methanesulfonamido]-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide (1423007-30-0) + pinacol vinylboronate (75927-49-0) → 6-[N-(3-chloro-4-vinylphenyl)methanesulfonamido]-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide (1423008-17-6)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; In 1,4-dioxane; water; at 80 ℃; for 16h;

Reference yield:

p-benzoquinone (106-51-4) → 6-[N-(3-chloro-4-vinylphenyl)methanesulfonamido]-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide (1423008-17-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: zinc(II) chloride / methanol; diethyl ether / 7.5 h / 75 - 140 °C / Inert atmosphere

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

3.1: nitric acid / chloroform / 1 h / -15 - 0 °C

4.1: boron trichloride / dichloromethane / 0.5 h / -15 °C / Inert atmosphere

5.1: triethylamine; dmap / dichloromethane / 0.83 h / 0 °C / Cooling with ice; Inert atmosphere

6.1: potassium fluoride; sodium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; water / 18 h / 100 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogenchloride; hydrogen / water; ethyl acetate / 16 h / 21 °C

8.1: triethylamine / dichloromethane / 2 h / 0 °C

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

10.1: triethylamine; HATU / dichloromethane / 1 h / 20 °C

10.2: 4 h / Inert atmosphere

11.1: potassium carbonate / water; 1,2-dimethoxyethane / 88 h / 20 - 100 °C / Sealed tube

12.1: hydrogen; 5 % platinum carbon sulfide / tetrahydrofuran; methanol / 40 h / 2068.65 Torr

13.1: hydrogen bromide / acetonitrile; water / 1 h / Cooling with ice

13.2: 1.58 h / Cooling with ice

13.3: 0.75 h / 60 °C

14.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; 1,4-dioxane / 16 h / 80 °C

With hydrogenchloride; dmap; potassium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium 10% on activated carbon; 5 % platinum carbon sulfide; water; hydrogen bromide; hydrogen; nitric acid; boron trichloride; sodium carbonate; potassium carbonate; caesium carbonate; triethylamine; HATU; sodium bromide; potassium hydroxide; zinc(II) chloride; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; chloroform; water; ethyl acetate; toluene; acetonitrile; 13.1: |Sandmeyer Reaction;

Reference yield:

methyl 2-(4-fluorophenyl)-5-hydroxy-1-benzofuran-3-carboxylate (691856-96-9) → 6-[N-(3-chloro-4-vinylphenyl)methanesulfonamido]-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide (1423008-17-6)

Guidance literature:

Multi-step reaction with 13 steps

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

2.1: nitric acid / chloroform / 1 h / -15 - 0 °C

3.1: boron trichloride / dichloromethane / 0.5 h / -15 °C / Inert atmosphere

4.1: triethylamine; dmap / dichloromethane / 0.83 h / 0 °C / Cooling with ice; Inert atmosphere

5.1: potassium fluoride; sodium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; water / 18 h / 100 °C / Inert atmosphere

6.1: palladium 10% on activated carbon; hydrogenchloride; hydrogen / water; ethyl acetate / 16 h / 21 °C

7.1: triethylamine / dichloromethane / 2 h / 0 °C

8.1: potassium hydroxide; water / ethanol / 1 h / Reflux

9.1: triethylamine; HATU / dichloromethane / 1 h / 20 °C

9.2: 4 h / Inert atmosphere

10.1: potassium carbonate / water; 1,2-dimethoxyethane / 88 h / 20 - 100 °C / Sealed tube

11.1: hydrogen; 5 % platinum carbon sulfide / tetrahydrofuran; methanol / 40 h / 2068.65 Torr

12.1: hydrogen bromide / acetonitrile; water / 1 h / Cooling with ice

12.2: 1.58 h / Cooling with ice

12.3: 0.75 h / 60 °C

13.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; 1,4-dioxane / 16 h / 80 °C

With hydrogenchloride; dmap; potassium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium 10% on activated carbon; 5 % platinum carbon sulfide; water; hydrogen bromide; hydrogen; nitric acid; boron trichloride; sodium carbonate; potassium carbonate; caesium carbonate; triethylamine; HATU; sodium bromide; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; chloroform; water; ethyl acetate; toluene; acetonitrile; 12.1: |Sandmeyer Reaction;

upstream raw materials:

p-benzoquinone

6-[N-(4-bromo-3-chlorophenyl)methanesulfonamido]-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

pinacol vinylboronate

methyl 2-(4-fluorophenyl)-5-hydroxy-1-benzofuran-3-carboxylate

Downstream raw materials:

6-(N-(3-chloro-4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)phenyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide

[2-(2-chloro-4-{N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)-1-benzofuran-6-yl]methanesulfonamido}phenyl)ethyl]boronic acid

6-[N-(3-chloro-4-formylphenyl)methanesulfonamido]-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

6-{N-[3-chloro-4-(1-hydroxyallyl)phenyl]methanesulfonamido}-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

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