N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(hydroxymethyl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide

Base Information

• Chemical Name: N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(hydroxymethyl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide
• CAS No.: 1383851-19-1
• Molecular Formula: C₂₇H₂₆FNO₅S
• Molecular Weight: 495.572
• Mol file: 1383851-19-1.mol

Synonyms:N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(hydroxymethyl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide

Chemical Property of N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(hydroxymethyl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(hydroxymethyl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide

There total 10 articles about N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(hydroxymethyl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide 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: 99.0%

ethyl 5-cyclopropyl-2-(4-fluorophenyl)-6-[(4-methoxybenzyl)(methylsulfonyl)amino]-1-benzofuran-3-carboxylate (1383851-18-0) → N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(hydroxymethyl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide (1383851-19-1)

Guidance literature:

ethyl 5-cyclopropyl-2-(4-fluorophenyl)-6-[(4-methoxybenzyl)(methylsulfonyl)amino]-1-benzofuran-3-carboxylate; With lithium aluminium tetrahydride; In tetrahydrofuran; at 10 - 20 ℃; for 2h; Inert atmosphere;

With water; sodium hydroxide; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

Reference yield:

1-(4-fluorophenyl)ethanone (403-42-9) → N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(hydroxymethyl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide (1383851-19-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: potassium tert-butylate / toluene / 78 °C / Inert atmosphere

1.2: 78 °C / Inert atmosphere

1.3: 78 °C / Inert atmosphere

2.1: zinc(II) chloride / tetrahydrofuran; toluene / 6 h / Reflux; Inert atmosphere

3.1: 1-methyl-pyrrolidin-2-one; caesium carbonate / 4 h / 50 °C / Inert atmosphere

4.1: nitric acid / chloroform / 1 h / 0 - 20 °C

5.1: boron trichloride / dichloromethane / 1 h / 0 - 20 °C

5.2: 20 °C

6.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h

7.1: potassium fluoride dihydrate; sodium bromide / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 18 h / 125 °C / Inert atmosphere; sealed vessel

8.1: iron; ammonium chloride / tetrahydrofuran; ethanol; water / 1.5 h / Inert atmosphere; Reflux

9.1: pyridine / dichloromethane / 3.33 h / 20 °C / Inert atmosphere

10.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 50 °C

11.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 10 - 20 °C / Inert atmosphere

11.2: 20 °C / Inert atmosphere

With pyridine; 1-methyl-pyrrolidin-2-one; dmap; lithium aluminium tetrahydride; potassium fluoride dihydrate; potassium tert-butylate; nitric acid; boron trichloride; iron; potassium carbonate; ammonium chloride; caesium carbonate; N-ethyl-N,N-diisopropylamine; sodium bromide; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene;

Reference yield:

ethyl 3-(4'-fluorophenyl)-3-oxopropionate (1999-00-4) → N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(hydroxymethyl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide (1383851-19-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: zinc(II) chloride / tetrahydrofuran; toluene / 6 h / Reflux; Inert atmosphere

2.1: 1-methyl-pyrrolidin-2-one; caesium carbonate / 4 h / 50 °C / Inert atmosphere

3.1: nitric acid / chloroform / 1 h / 0 - 20 °C

4.1: boron trichloride / dichloromethane / 1 h / 0 - 20 °C

4.2: 20 °C

5.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h

6.1: potassium fluoride dihydrate; sodium bromide / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 18 h / 125 °C / Inert atmosphere; sealed vessel

7.1: iron; ammonium chloride / tetrahydrofuran; ethanol; water / 1.5 h / Inert atmosphere; Reflux

8.1: pyridine / dichloromethane / 3.33 h / 20 °C / Inert atmosphere

9.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 50 °C

10.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 10 - 20 °C / Inert atmosphere

10.2: 20 °C / Inert atmosphere

With pyridine; 1-methyl-pyrrolidin-2-one; dmap; lithium aluminium tetrahydride; potassium fluoride dihydrate; nitric acid; boron trichloride; iron; potassium carbonate; ammonium chloride; caesium carbonate; N-ethyl-N,N-diisopropylamine; sodium bromide; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

1-(4-fluorophenyl)ethanone

ethyl 3-(4'-fluorophenyl)-3-oxopropionate

ethyl 2-(4-fluorophenyl)-5-hydroxy-6-nitrobenzofuran-3-carboxylate

ethyl 2-(4-fluorophenyl)-5-isopropoxy-6-nitrobenzofuran-3-carboxylate

Downstream raw materials:

4-{[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl](methylsulfonyl)amino}butanoic acid

N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl]-N-[2-(ethylsulfonyl)ethyl]methanesulfonamide

4-{[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl](methylsulfonyl)amino } butanamide

N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl]-N-(2-hydroxyethyl)methanesulfonamide

Refernces