5-cyclopropyl-2-(4-fluorophenyl)-6-[{[(3S)-1-hydroxy-3-methyl-1,3-dihydro-2,1-benzoxaborol-5-yl]methyl}(methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide

Base Information

• Chemical Name: 5-cyclopropyl-2-(4-fluorophenyl)-6-[{[(3S)-1-hydroxy-3-methyl-1,3-dihydro-2,1-benzoxaborol-5-yl]methyl}(methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide
• CAS No.: 1378427-83-8
• Molecular Formula: C₂₉H₂₈BFN₂O₆S
• Molecular Weight: 562.427
• Mol file: 1378427-83-8.mol

Synonyms:

Chemical Property of 5-cyclopropyl-2-(4-fluorophenyl)-6-[{[(3S)-1-hydroxy-3-methyl-1,3-dihydro-2,1-benzoxaborol-5-yl]methyl}(methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-cyclopropyl-2-(4-fluorophenyl)-6-[{[(3S)-1-hydroxy-3-methyl-1,3-dihydro-2,1-benzoxaborol-5-yl]methyl}(methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide

There total 20 articles about 5-cyclopropyl-2-(4-fluorophenyl)-6-[{[(3S)-1-hydroxy-3-methyl-1,3-dihydro-2,1-benzoxaborol-5-yl]methyl}(methylsulfonyl)amino]-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:

p-benzoquinone (106-51-4) → 5-cyclopropyl-2-(4-fluorophenyl)-6-[{[(3S)-1-hydroxy-3-methyl-1,3-dihydro-2,1-benzoxaborol-5-yl]methyl}(methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide (1378427-83-8) + 5-cyclopropyl-2-(4-fluorophenyl)-6-[{[(3R)-1-hydroxy-3-methyl-1,3-dihydro-2,1-benzoxaborol-5-yl]methyl}(methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide (1378427-84-9)

Guidance literature:

Multi-step reaction with 14 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 / acetonitrile / 3 h / 80 °C

12.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 90 °C

13.1: hydrogenchloride / water / 3 h / 65 °C

14.1: OZ column / carbon dioxide; methanol / Resolution of racemate

With hydrogenchloride; dmap; potassium fluoride; water; hydrogen; nitric acid; potassium acetate; boron trichloride; potassium carbonate; caesium carbonate; triethylamine; HATU; 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; carbon dioxide; water; ethyl acetate; toluene; acetonitrile;

Reference yield:

5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (691856-35-6) → 5-cyclopropyl-2-(4-fluorophenyl)-6-[{[(3S)-1-hydroxy-3-methyl-1,3-dihydro-2,1-benzoxaborol-5-yl]methyl}(methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide (1378427-83-8) + 5-cyclopropyl-2-(4-fluorophenyl)-6-[{[(3R)-1-hydroxy-3-methyl-1,3-dihydro-2,1-benzoxaborol-5-yl]methyl}(methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide (1378427-84-9)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / acetonitrile / 3 h / 80 °C

2: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 90 °C

3: hydrogenchloride / water / 3 h / 65 °C

4: OZ column / carbon dioxide; methanol / Resolution of racemate

With hydrogenchloride; potassium acetate; potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; methanol; carbon dioxide; water; acetonitrile;

Reference yield:

methyl 4-fluorobenzoyl acetate (63131-29-3) → 5-cyclopropyl-2-(4-fluorophenyl)-6-[{[(3S)-1-hydroxy-3-methyl-1,3-dihydro-2,1-benzoxaborol-5-yl]methyl}(methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide (1378427-83-8) + 5-cyclopropyl-2-(4-fluorophenyl)-6-[{[(3R)-1-hydroxy-3-methyl-1,3-dihydro-2,1-benzoxaborol-5-yl]methyl}(methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide (1378427-84-9)

Guidance literature:

Multi-step reaction with 14 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 / acetonitrile / 3 h / 80 °C

12.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 90 °C

13.1: hydrogenchloride / water / 3 h / 65 °C

14.1: OZ column / carbon dioxide; methanol / Resolution of racemate

With hydrogenchloride; dmap; potassium fluoride; water; hydrogen; nitric acid; potassium acetate; boron trichloride; potassium carbonate; caesium carbonate; triethylamine; HATU; 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; carbon dioxide; water; ethyl acetate; toluene; acetonitrile;

upstream raw materials:

methyl 4-fluorobenzoyl acetate

p-benzoquinone

1-(2-bromo-5-methylphenyl)ethanone

5-cyclopropyl-2-(4-fluorophenyl)-6-[(methylsulfonyl)amino]-1-benzofuran-3-carboxylic acid