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

Base Information

• Chemical Name: methyl 3-chloro-5-((N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• CAS No.: 1378431-68-5
• Molecular Formula: C₃₅H₃₇BClFN₂O₈S
• Molecular Weight: 711.016
• Mol file: 1378431-68-5.mol

Synonyms:methyl 3-chloro-5-((N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Chemical Property of methyl 3-chloro-5-((N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-chloro-5-((N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

There total 17 articles about methyl 3-chloro-5-((N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 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: 15.0%

methyl 2-bromo-3-chloro-5-((N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)methylsulfonamido)methyl)benzoate (1378431-66-3) + bis(pinacol)diborane (73183-34-3) → methyl 3-chloro-5-((N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1378431-68-5)

Guidance literature:

With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; at 100 ℃; Inert atmosphere;

Reference yield:

methyl 4-fluorobenzoyl acetate (63131-29-3) → methyl 3-chloro-5-((N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1378431-68-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: zinc(II) chloride / diethyl ether; methanol / 7.5 h / 75 - 115 °C / Inert atmosphere

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

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

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

4.2: Cooling with ice

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

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

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

8.1: triethylamine / dichloromethane / 2 h / 0 °C / Cooling with ice

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

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

10.2: 4 h / 20 °C / Inert atmosphere

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

12.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 100 °C / Inert atmosphere

With hydrogenchloride; dmap; potassium fluoride; water; hydrogen; nitric acid; potassium acetate; boron trichloride; potassium carbonate; caesium carbonate; triethylamine; HATU; potassium iodide; sodium bromide; potassium hydroxide; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium 10% on activated carbon; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

Reference yield:

p-benzoquinone (106-51-4) → methyl 3-chloro-5-((N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1378431-68-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: zinc(II) chloride / diethyl ether; methanol / 7.5 h / 75 - 115 °C / Inert atmosphere

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

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

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

4.2: Cooling with ice

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

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

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

8.1: triethylamine / dichloromethane / 2 h / 0 °C / Cooling with ice

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

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

10.2: 4 h / 20 °C / Inert atmosphere

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

12.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 100 °C / Inert atmosphere

With hydrogenchloride; dmap; potassium fluoride; water; hydrogen; nitric acid; potassium acetate; boron trichloride; potassium carbonate; caesium carbonate; triethylamine; HATU; potassium iodide; sodium bromide; potassium hydroxide; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium 10% on activated carbon; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

upstream raw materials:

methyl 4-fluorobenzoyl acetate

methyl 2-bromo-3-chloro-5-((N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)methylsulfonamido)methyl)benzoate

bis(pinacol)diborane

p-benzoquinone

Downstream raw materials:

6-(N-((7-chloro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide

Refernces