2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide

Base Information

• Chemical Name: 2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide
• CAS No.: 1621705-30-3
• Molecular Formula: C₂₅H₂₉BF₂N₂O₆S
• Molecular Weight: 534.389
• Mol file: 1621705-30-3.mol

Synonyms:2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide

Chemical Property of 2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide

There total 12 articles about 2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)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: 55.0%

5-bromo-2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (1621705-29-0) + bis(pinacol)diborane (73183-34-3) → 2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (1621705-30-3)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; water; at 130 ℃; for 3h; Inert atmosphere;

Reference yield:

5-bromosalicyclaldehyde (1761-61-1) → 2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (1621705-30-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: tetrafluoroboric acid diethyl ether / dichloromethane / 38 °C

2.1: nitric acid / chloroform / 2.5 h / -20 - 0 °C

3.1: iron; ammonium chloride / methanol; tetrahydrofuran; water / 3 h / Reflux

4.1: lithium hydroxide monohydrate; water / 1,4-dioxane / 2 h / Reflux

5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 2 h / 25 °C

5.2: 2 h

6.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

6.2: 1 h / -78 °C

7.1: N-iodo-succinimide / acetonitrile / 0 - 25 °C

8.1: pyridine / 1.5 h / 0 - 25 °C

9.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 0 - 80 °C / Inert atmosphere

10.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere

11.1: diethylamino-sulfur trifluoride / dichloromethane / 5 h / -78 - 25 °C

12.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / water; 1,4-dioxane / 3 h / 130 °C / Inert atmosphere

With pyridine; tetrafluoroboric acid diethyl ether; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-iodo-succinimide; lithium hydroxide monohydrate; diethylamino-sulfur trifluoride; water; nitric acid; potassium acetate; iron; sodium carbonate; potassium carbonate; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; 10.1: |Suzuki Coupling;

Reference yield:

5-bromo-2-(4-formylphenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (1621705-28-9) → 2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (1621705-30-3)

Guidance literature:

Multi-step reaction with 2 steps

1: diethylamino-sulfur trifluoride / dichloromethane / 5 h / -78 - 25 °C

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / water; 1,4-dioxane / 3 h / 130 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; diethylamino-sulfur trifluoride; potassium acetate; In 1,4-dioxane; dichloromethane; water;

upstream raw materials:

5-bromo-2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

bis(pinacol)diborane

5-bromo-2-(4-formylphenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

5-bromosalicyclaldehyde

Downstream raw materials:

2-(4-(difluoromethyl)phenyl)-5-(11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

2-(4-(difluoromethyl)phenyl)-5-(11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide