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

Base Information

• Chemical Name: (2-chloro-4-{N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)-1-benzofuran-6-yl]methanesulfonamido}phenyl)boronic acid
• CAS No.: 1423007-27-5
• Molecular Formula: C₂₆H₂₃BClFN₂O₆S
• Molecular Weight: 556.807
• Mol file: 1423007-27-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about (2-chloro-4-{N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)-1-benzofuran-6-yl]methanesulfonamido}phenyl)boronic acid 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: 74.0%

6-[N-(4-bromo-3-chlorophenyl)methanesulfonamido]-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide (1423007-30-0) + bis(pinacol)diborane (73183-34-3) → (2-chloro-4-{N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)-1-benzofuran-6-yl]methanesulfonamido}phenyl)boronic acid (1423007-27-5)

Guidance literature:

6-[N-(4-bromo-3-chlorophenyl)methanesulfonamido]-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide; bis(pinacol)diborane; With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 80 ℃; for 4.16667h; Inert atmosphere; Sealed tube;

With hydrogenchloride; sodium periodate; In tetrahydrofuran; water; at 0 - 20 ℃; for 18h;

Reference yield:

C32H33BClFN2O6S → (2-chloro-4-{N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)-1-benzofuran-6-yl]methanesulfonamido}phenyl)boronic acid (1423007-27-5)

Guidance literature:

C₃₂H₃₃BClFN₂O₆S; With hydrogenchloride; sodium periodate; water; In tetrahydrofuran; at 0 - 20 ℃; for 18h; Inert atmosphere;

With hydrogenchloride; In water; acetonitrile; at 20 ℃; for 2.33333h;

Reference yield:

5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (691856-35-6) → (2-chloro-4-{N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)-1-benzofuran-6-yl]methanesulfonamido}phenyl)boronic acid (1423007-27-5)

Guidance literature:

Multi-step reaction with 4 steps

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

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

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

3.2: 1.58 h / Cooling with ice

3.3: 0.75 h / 60 °C

4.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 4.17 h / 80 °C / Inert atmosphere; Sealed tube

4.2: 18 h / 0 - 20 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; 5 % platinum carbon sulfide; hydrogen bromide; hydrogen; potassium acetate; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; water; acetonitrile; 3.1: |Sandmeyer Reaction;

upstream raw materials:

p-benzoquinone

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

methyl 2-(4-fluorophenyl)-5-[(1-methylethyl)oxy]-1-benzofuran-3-carboxylate

methyl 2-(4-fluorophenyl)-5-[(1-methylethyl)oxy]-6-nitro-1-benzofuran-3-carboxylate

Refernces

• 1、 -. "THERAPEUTIC METHODS". . . Retrieved 2013/03/26.