methyl 5-{[[3-(aminocarbonyl)-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-6-yl](methylsulfonyl)amino]methyl}-2-bromo-3-fluorobenzoate

Base Information

• Chemical Name: methyl 5-{[[3-(aminocarbonyl)-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-6-yl](methylsulfonyl)amino]methyl}-2-bromo-3-fluorobenzoate
• CAS No.: 1378432-26-8
• Molecular Formula: C₂₈H₂₃BrF₂N₂O₆S
• Molecular Weight: 633.467
• Mol file: 1378432-26-8.mol

Synonyms:methyl 5-{[[3-(aminocarbonyl)-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-6-yl](methylsulfonyl)amino]methyl}-2-bromo-3-fluorobenzoate

Chemical Property of methyl 5-{[[3-(aminocarbonyl)-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-6-yl](methylsulfonyl)amino]methyl}-2-bromo-3-fluorobenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-{[[3-(aminocarbonyl)-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-6-yl](methylsulfonyl)amino]methyl}-2-bromo-3-fluorobenzoate

There total 12 articles about methyl 5-{[[3-(aminocarbonyl)-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-6-yl](methylsulfonyl)amino]methyl}-2-bromo-3-fluorobenzoate 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: 95.0%

methyl 2-bromo-5-(bromomethyl)-3-fluorobenzoate (1378431-05-0) + 5-cyclopropyl-2-(4-fluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxamide (1331945-03-9) → methyl 5-{[[3-(aminocarbonyl)-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-6-yl](methylsulfonyl)amino]methyl}-2-bromo-3-fluorobenzoate (1378432-26-8)

Guidance literature:

With potassium carbonate; sodium iodide; In N,N-dimethyl-formamide; at 30 ℃; for 0.666667h;

Reference yield:

methyl 4-fluorobenzoyl acetate (63131-29-3) → methyl 5-{[[3-(aminocarbonyl)-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-6-yl](methylsulfonyl)amino]methyl}-2-bromo-3-fluorobenzoate (1378432-26-8)

Guidance literature:

Multi-step reaction with 11 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: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 20 °C

10.2: 2 h

11.1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 0.67 h / 30 °C

With hydrogenchloride; dmap; potassium fluoride; water; hydrogen; nitric acid; boron trichloride; potassium carbonate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium iodide; sodium bromide; potassium hydroxide; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; In 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 5-{[[3-(aminocarbonyl)-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-6-yl](methylsulfonyl)amino]methyl}-2-bromo-3-fluorobenzoate (1378432-26-8)

Guidance literature:

Multi-step reaction with 11 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: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 20 °C

10.2: 2 h

11.1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 0.67 h / 30 °C

With hydrogenchloride; dmap; potassium fluoride; water; hydrogen; nitric acid; boron trichloride; potassium carbonate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium iodide; sodium bromide; potassium hydroxide; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; In 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

p-benzoquinone

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

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

Downstream raw materials:

6-[{[4-bromo-3-fluoro-5-(hydroxymethyl)phenyl]methyl}(methylsulfonyl)amino]-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-3-carboxamide

6-[{[4-bromo-3-fluoro-5-({[(methyloxy)methyl]oxy}methyl)phenyl]methyl}(methylsulfonyl)amino]-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-3-carboxamide

5-cyclopropyl-6-[{[3-fluoro-5-({[(methyloxy)methyl]oxy}methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}(methylsulfonyl)amino]-2-(4-fluorophenyl)-1-benzofuran-3-carboxamide

5-cyclopropyl-6-[[(7-fluoro-1-hydroxy-1,3-dihydro-2,1-benzoxaborol-5-yl)methyl](methylsulfonyl)amino]-2-(4-fluorophenyl)-1-benzofuran-3-carboxamide