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Technology Process of 5-cyclopropyl-2-(4-fluorophenyl)-6-[[(2-hydroxy-1,2-oxaborinan-5-yl)methyl](methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide

5-cyclopropyl-2-(4-fluorophenyl)-6-[[(2-hydroxy-1,2-oxaborinan-5-yl)methyl](methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide

Base Information
  • Chemical Name:5-cyclopropyl-2-(4-fluorophenyl)-6-[[(2-hydroxy-1,2-oxaborinan-5-yl)methyl](methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide
  • CAS No.:1378427-37-2
  • Molecular Formula:C25H28BFN2O6S
  • Molecular Weight:514.383
  • Hs Code.:
5-cyclopropyl-2-(4-fluorophenyl)-6-[[(2-hydroxy-1,2-oxaborinan-5-yl)methyl](methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide

Synonyms:5-cyclopropyl-2-(4-fluorophenyl)-6-[[(2-hydroxy-1,2-oxaborinan-5-yl)methyl](methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide

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Chemical Property of 5-cyclopropyl-2-(4-fluorophenyl)-6-[[(2-hydroxy-1,2-oxaborinan-5-yl)methyl](methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide
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Technology Process of 5-cyclopropyl-2-(4-fluorophenyl)-6-[[(2-hydroxy-1,2-oxaborinan-5-yl)methyl](methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide

There total 16 articles about 5-cyclopropyl-2-(4-fluorophenyl)-6-[[(2-hydroxy-1,2-oxaborinan-5-yl)methyl](methylsulfonyl)amino]-N-methyl-1-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: 22.6%

6-(N-(2-(benzyloxymethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide
1378429-17-4

6-(N-(2-(benzyloxymethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide

5-cyclopropyl-2-(4-fluorophenyl)-6-[[(2-hydroxy-1,2-oxaborinan-5-yl)methyl](methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide
1378427-37-2

5-cyclopropyl-2-(4-fluorophenyl)-6-[[(2-hydroxy-1,2-oxaborinan-5-yl)methyl](methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide

Guidance literature:
With hydrogen; palladium 10% on activated carbon; In tetrahydrofuran; at 20 ℃; for 6h; under 3102.97 Torr;

Reference yield:

methyl 4-fluorobenzoyl acetate
63131-29-3

methyl 4-fluorobenzoyl acetate

5-cyclopropyl-2-(4-fluorophenyl)-6-[[(2-hydroxy-1,2-oxaborinan-5-yl)methyl](methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide
1378427-37-2

5-cyclopropyl-2-(4-fluorophenyl)-6-[[(2-hydroxy-1,2-oxaborinan-5-yl)methyl](methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide

Guidance literature:
Multi-step reaction with 13 steps
1.1: zinc(II) chloride / diethyl ether; methanol / 7.5 h / 75 - 115 °C / Inert atmosphere
2.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 20 h / 60 °C / Inert atmosphere
3.1: nitric acid / chloroform / 1 h / -15 - 0 °C
4.1: boron trichloride / dichloromethane / 0.5 h / -15 °C / Inert atmosphere
4.2: Cooling with ice
5.1: dmap; triethylamine / dichloromethane / 0.83 h / 0 °C / Inert atmosphere
6.1: potassium fluoride; sodium bromide / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 18 h / 100 °C / Inert atmosphere
7.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethyl acetate; water / 16 h / 21 °C
8.1: triethylamine / dichloromethane / 2 h / 0 °C / Cooling with ice
9.1: potassium hydroxide; water / ethanol / 1 h / Reflux
10.1: triethylamine; HATU / dichloromethane / 1 h / 20 °C / Inert atmosphere
10.2: 4 h / 20 °C / Inert atmosphere
11.1: N,N-dimethyl-formamide / 48 h / 80 °C / Inert atmosphere
12.1: carbonylbis(triphenylphosphine)rhodium(1)chloride / tetrahydrofuran / 3 h / Inert atmosphere
13.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / 3102.97 Torr
With hydrogenchloride; dmap; potassium fluoride; water; hydrogen; nitric acid; boron trichloride; caesium carbonate; triethylamine; HATU; sodium bromide; potassium hydroxide; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon; carbonylbis(triphenylphosphine)rhodium(1)chloride; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

Reference yield:

p-benzoquinone
106-51-4

p-benzoquinone

5-cyclopropyl-2-(4-fluorophenyl)-6-[[(2-hydroxy-1,2-oxaborinan-5-yl)methyl](methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide
1378427-37-2

5-cyclopropyl-2-(4-fluorophenyl)-6-[[(2-hydroxy-1,2-oxaborinan-5-yl)methyl](methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide

Guidance literature:
Multi-step reaction with 13 steps
1.1: zinc(II) chloride / diethyl ether; methanol / 7.5 h / 75 - 115 °C / Inert atmosphere
2.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 20 h / 60 °C / Inert atmosphere
3.1: nitric acid / chloroform / 1 h / -15 - 0 °C
4.1: boron trichloride / dichloromethane / 0.5 h / -15 °C / Inert atmosphere
4.2: Cooling with ice
5.1: dmap; triethylamine / dichloromethane / 0.83 h / 0 °C / Inert atmosphere
6.1: potassium fluoride; sodium bromide / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 18 h / 100 °C / Inert atmosphere
7.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethyl acetate; water / 16 h / 21 °C
8.1: triethylamine / dichloromethane / 2 h / 0 °C / Cooling with ice
9.1: potassium hydroxide; water / ethanol / 1 h / Reflux
10.1: triethylamine; HATU / dichloromethane / 1 h / 20 °C / Inert atmosphere
10.2: 4 h / 20 °C / Inert atmosphere
11.1: N,N-dimethyl-formamide / 48 h / 80 °C / Inert atmosphere
12.1: carbonylbis(triphenylphosphine)rhodium(1)chloride / tetrahydrofuran / 3 h / Inert atmosphere
13.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / 3102.97 Torr
With hydrogenchloride; dmap; potassium fluoride; water; hydrogen; nitric acid; boron trichloride; caesium carbonate; triethylamine; HATU; sodium bromide; potassium hydroxide; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon; carbonylbis(triphenylphosphine)rhodium(1)chloride; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
upstream raw materials:

methyl 4-fluorobenzoyl acetate

p-benzoquinone

5-cyclopropyl-2-(4-fluorophenyl)-6-[(methylsulfonyl)amino]-1-benzofuran-3-carboxylic acid

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

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