5-cyclopropyl-6-(N-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)methylsulfonamido)-N-methyl-2-(4-(trifluoromethyl)phenyl)benzofuran-3-carboxamide

Base Information

• Chemical Name: 5-cyclopropyl-6-(N-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)methylsulfonamido)-N-methyl-2-(4-(trifluoromethyl)phenyl)benzofuran-3-carboxamide
• CAS No.: 1378427-71-4
• Molecular Formula: C₂₉H₂₆BF₃N₂O₆S
• Molecular Weight: 598.407

Synonyms:5-cyclopropyl-6-(N-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)methylsulfonamido)-N-methyl-2-(4-(trifluoromethyl)phenyl)benzofuran-3-carboxamide

Chemical Property of 5-cyclopropyl-6-(N-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)methylsulfonamido)-N-methyl-2-(4-(trifluoromethyl)phenyl)benzofuran-3-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-cyclopropyl-6-(N-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)methylsulfonamido)-N-methyl-2-(4-(trifluoromethyl)phenyl)benzofuran-3-carboxamide

There total 14 articles about 5-cyclopropyl-6-(N-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)methylsulfonamido)-N-methyl-2-(4-(trifluoromethyl)phenyl)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: 37.0%

methyl 5-((N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(4-(trifluoromethyl)phenyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1378430-81-9) → 5-cyclopropyl-6-(N-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)methylsulfonamido)-N-methyl-2-(4-(trifluoromethyl)phenyl)benzofuran-3-carboxamide (1378427-71-4)

Guidance literature:

methyl 5-((N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(4-(trifluoromethyl)phenyl)benzofuran-6-yl)methylsulfonamido)methyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate; With lithium borohydride; In tetrahydrofuran; at -5 ℃; for 0.25h;

With water; In tetrahydrofuran; Cooling with ice;

Reference yield:

p-benzoquinone (106-51-4) → 5-cyclopropyl-6-(N-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)methylsulfonamido)-N-methyl-2-(4-(trifluoromethyl)phenyl)benzofuran-3-carboxamide (1378427-71-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: zinc(II) chloride / ethanol; tert-butyl methyl ether / 2 h / 75 - 95 °C / Inert atmosphere

2.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 20 h / 60 °C

3.1: nitric acid / chloroform / 2.5 h / 0 °C / Cooling with ice

4.1: boron trichloride / dichloromethane / 0.33 h / Cooling with ice; Inert atmosphere

4.2: Cooling with ice

5.1: dmap; triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

6.1: potassium fluoride; sodium bromide / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; water / 20 h / Inert atmosphere; Reflux

7.1: hydrogen; [({2-[{5-cyclopropyl-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}(methylsulfonyl)amino]ethyl}oxy)methyl]boronic acid / palladium 10% on activated carbon / ethyl acetate / 8 h / 20 °C / 3000.3 Torr

8.1: triethylamine / dichloromethane / 2 h / -15 - 20 °C

9.1: potassium hydroxide; water / ethanol / 1 h / Reflux; Inert atmosphere

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 / acetonitrile / 70 °C / Inert atmosphere

12.1: triethylamine / CyJohnPhos; palladium diacetate / 1,4-dioxane / 100 °C / Inert atmosphere

13.1: lithium borohydride / tetrahydrofuran / 0.25 h / -5 °C

13.2: Cooling with ice

With dmap; potassium fluoride; lithium borohydride; [({2-[{5-cyclopropyl-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}(methylsulfonyl)amino]ethyl}oxy)methyl]boronic acid; water; hydrogen; nitric acid; boron trichloride; potassium carbonate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium bromide; potassium hydroxide; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; palladium diacetate; CyJohnPhos; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; tert-butyl methyl ether; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

ethyl (4-chlorobenzoyl)acetate (2881-63-2) → 5-cyclopropyl-6-(N-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)methyl)methylsulfonamido)-N-methyl-2-(4-(trifluoromethyl)phenyl)benzofuran-3-carboxamide (1378427-71-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: zinc(II) chloride / ethanol; tert-butyl methyl ether / 2 h / 75 - 95 °C / Inert atmosphere

2.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 20 h / 60 °C

3.1: nitric acid / chloroform / 2.5 h / 0 °C / Cooling with ice

4.1: boron trichloride / dichloromethane / 0.33 h / Cooling with ice; Inert atmosphere

4.2: Cooling with ice

5.1: dmap; triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

6.1: potassium fluoride; sodium bromide / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; water / 20 h / Inert atmosphere; Reflux

7.1: hydrogen; [({2-[{5-cyclopropyl-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}(methylsulfonyl)amino]ethyl}oxy)methyl]boronic acid / palladium 10% on activated carbon / ethyl acetate / 8 h / 20 °C / 3000.3 Torr

8.1: triethylamine / dichloromethane / 2 h / -15 - 20 °C

9.1: potassium hydroxide; water / ethanol / 1 h / Reflux; Inert atmosphere

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 / acetonitrile / 70 °C / Inert atmosphere

12.1: triethylamine / CyJohnPhos; palladium diacetate / 1,4-dioxane / 100 °C / Inert atmosphere

13.1: lithium borohydride / tetrahydrofuran / 0.25 h / -5 °C

13.2: Cooling with ice

With dmap; potassium fluoride; lithium borohydride; [({2-[{5-cyclopropyl-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}(methylsulfonyl)amino]ethyl}oxy)methyl]boronic acid; water; hydrogen; nitric acid; boron trichloride; potassium carbonate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium bromide; potassium hydroxide; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; palladium diacetate; CyJohnPhos; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; tert-butyl methyl ether; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

p-benzoquinone

ethyl (4-chlorobenzoyl)acetate

ethyl 2-(4-chlorophenyl)-5-hydroxybenzofuran-3-carboxylate

ethyl 2-(4-chlorophenyl)-5-isopropoxybenzofuran-3-carboxylate

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