6-(N-(2,2-difluoroethyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide

Base Information

• Chemical Name: 6-(N-(2,2-difluoroethyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide
• CAS No.: 1427035-46-8
• Molecular Formula: C₂₅H₂₈BF₃N₂O₆S
• Molecular Weight: 552.379
• Mol file: 1427035-46-8.mol

Synonyms:6-(N-(2,2-difluoroethyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide

Chemical Property of 6-(N-(2,2-difluoroethyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methyl-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 6-(N-(2,2-difluoroethyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide

There total 8 articles about 6-(N-(2,2-difluoroethyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methyl-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: 74.0%

5-bromo-6-(N-(2,2-difluoroethyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (1427035-45-7) + bis(pinacol)diborane (73183-34-3) → 6-(N-(2,2-difluoroethyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (1427035-46-8)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In water; at 80 ℃; for 4h;

Reference yield:

ethyl 6-amino-5-bromo-2-(4-fluorophenyl)benzofuran-3-carboxylate (1333340-15-0) → 6-(N-(2,2-difluoroethyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (1427035-46-8)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / dichloromethane / 0 - 20 °C

2: water; lithium hydroxide monohydrate / 1,4-dioxane / 3 h / 100 °C

3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 2 h / 20 °C

4: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 2 h / 80 °C / Reflux

5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane; water / 4 h / 80 °C / Inert atmosphere; Reflux

With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium hydroxide monohydrate; water; potassium acetate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium iodide; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

5-bromo-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (1333244-33-9) → 6-(N-(2,2-difluoroethyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (1427035-46-8)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 2 h / 80 °C / Reflux

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane; water / 4 h / 80 °C / Inert atmosphere; Reflux

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; potassium carbonate; potassium iodide; In 1,4-dioxane; water; N,N-dimethyl-formamide;

upstream raw materials:

5-bromo-6-(N-(2,2-difluoroethyl)methylsulfonamido)-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide

bis(pinacol)diborane

ethyl 6-amino-5-bromo-2-(4-fluorophenyl)benzofuran-3-carboxylate

5-bromo-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide