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

Base Information

• Chemical Name: 5-bromo-2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide
• CAS No.: 1621705-29-0
• Molecular Formula: C₁₉H₁₇BrF₂N₂O₄S
• Molecular Weight: 487.322
• Mol file: 1621705-29-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about 5-bromo-2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)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: 50.0%

5-bromo-2-(4-formylphenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (1621705-28-9) → 5-bromo-2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (1621705-29-0)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; at -78 - 254 ℃; for 5h;

Reference yield:

5-bromosalicyclaldehyde (1761-61-1) → 5-bromo-2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (1621705-29-0)

Guidance literature:

Multi-step reaction with 11 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

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; 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:

ethyl 5-bromo-1-benzofuran-3-carboxylate (137242-41-2) → 5-bromo-2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (1621705-29-0)

Guidance literature:

Multi-step reaction with 10 steps

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

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

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

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

4.2: 2 h

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

5.2: 1 h / -78 °C

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

7.1: pyridine / 1.5 h / 0 - 25 °C

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

9.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere

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

With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-iodo-succinimide; lithium hydroxide monohydrate; diethylamino-sulfur trifluoride; water; nitric acid; 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; 9.1: |Suzuki Coupling;

upstream raw materials:

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

5-bromosalicyclaldehyde

ethyl 5-bromo-1-benzofuran-3-carboxylate

ethyl 5-bromo-6-nitrobenzofuran-3-carboxylate

Downstream raw materials:

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

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