5-cyclopropyl-2-(4-fluorophenyl)-6-(N-((2-hydroxy-1,2-oxaborolan-4-yl)methyl)-2-methylpropylsulfonamido)-N-methylbenzofuran-3-carboxamide

Base Information

• Chemical Name: 5-cyclopropyl-2-(4-fluorophenyl)-6-(N-((2-hydroxy-1,2-oxaborolan-4-yl)methyl)-2-methylpropylsulfonamido)-N-methylbenzofuran-3-carboxamide
• CAS No.: 1378427-48-5
• Molecular Formula: C₂₇H₃₂BFN₂O₆S
• Molecular Weight: 542.436
• Mol file: 1378427-48-5.mol

Synonyms:5-cyclopropyl-2-(4-fluorophenyl)-6-(N-((2-hydroxy-1,2-oxaborolan-4-yl)methyl)-2-methylpropylsulfonamido)-N-methylbenzofuran-3-carboxamide

Chemical Property of 5-cyclopropyl-2-(4-fluorophenyl)-6-(N-((2-hydroxy-1,2-oxaborolan-4-yl)methyl)-2-methylpropylsulfonamido)-N-methylbenzofuran-3-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-cyclopropyl-2-(4-fluorophenyl)-6-(N-((2-hydroxy-1,2-oxaborolan-4-yl)methyl)-2-methylpropylsulfonamido)-N-methylbenzofuran-3-carboxamide

There total 6 articles about 5-cyclopropyl-2-(4-fluorophenyl)-6-(N-((2-hydroxy-1,2-oxaborolan-4-yl)methyl)-2-methylpropylsulfonamido)-N-methylbenzofuran-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: 16.0%

6-(N-(3-(benzyloxy)-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)propyl)-2-methylpropylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (1378429-53-8) → 5-cyclopropyl-2-(4-fluorophenyl)-6-(N-((2-hydroxy-1,2-oxaborolan-4-yl)methyl)-2-methylpropylsulfonamido)-N-methylbenzofuran-3-carboxamide (1378427-48-5)

Guidance literature:

6-(N-(3-(benzyloxy)-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)propyl)-2-methylpropylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide; With hydrogen; palladium 10% on activated carbon; In tetrahydrofuran; at 20 ℃; for 16h; under 2585.81 Torr;

With hydrogenchloride; In tetrahydrofuran; water;

Reference yield:

ethyl 6-amino-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylate (691857-53-1) → 5-cyclopropyl-2-(4-fluorophenyl)-6-(N-((2-hydroxy-1,2-oxaborolan-4-yl)methyl)-2-methylpropylsulfonamido)-N-methylbenzofuran-3-carboxamide (1378427-48-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / dichloromethane / 1 h / -15 - 20 °C / Inert atmosphere

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

3.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 21 °C

3.2: 2 h

4.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere

5.1: carbonylbis(triphenylphosphine)rhodium⁽¹⁾chloride / tetrahydrofuran / 3 h / Inert atmosphere

6.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 16 h / 20 °C / 2585.81 Torr

6.2: PS-benzene boronic acid

With water; hydrogen; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; potassium iodide; potassium hydroxide; palladium 10% on activated carbon; carbonylbis(triphenylphosphine)rhodium⁽¹⁾chloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

ethyl 5-cyclopropyl-2-(4-fluorophenyl)-6-(2-methyl-N-(isobutylsulfonyl)propylsulfonamido)benzofuran-3-carboxylate → 5-cyclopropyl-2-(4-fluorophenyl)-6-(N-((2-hydroxy-1,2-oxaborolan-4-yl)methyl)-2-methylpropylsulfonamido)-N-methylbenzofuran-3-carboxamide (1378427-48-5)

Guidance literature:

Multi-step reaction with 5 steps

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

2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 21 °C

2.2: 2 h

3.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere

4.1: carbonylbis(triphenylphosphine)rhodium⁽¹⁾chloride / tetrahydrofuran / 3 h / Inert atmosphere

5.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 16 h / 20 °C / 2585.81 Torr

5.2: PS-benzene boronic acid

With water; hydrogen; potassium carbonate; N-ethyl-N,N-diisopropylamine; HATU; potassium iodide; potassium hydroxide; palladium 10% on activated carbon; carbonylbis(triphenylphosphine)rhodium⁽¹⁾chloride; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

upstream raw materials:

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

5-cyclopropyl-2-(4-fluorophenyl)-6-(2-methylpropylsulfonamido)benzofuran-3-carboxylic acid

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

6-(N-(2-(benzyloxymethyl)allyl)-2-methylpropylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide