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

Base Information

• Chemical Name: methyl 4-{[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl](methylsulfonyl)amino}butanoate
• CAS No.: 1383851-40-8
• Molecular Formula: C₂₆H₂₆FN₃O₅S
• Molecular Weight: 511.574

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

Chemical Property of methyl 4-{[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl](methylsulfonyl)amino}butanoate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of methyl 4-{[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl](methylsulfonyl)amino}butanoate

There total 16 articles about methyl 4-{[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl](methylsulfonyl)amino}butanoate 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: 94.0%

Ethyl 4-bromobutyrate (2969-81-5) + N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl]methanesulfonamide (1383851-15-7) → methyl 4-{[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl](methylsulfonyl)amino}butanoate (1383851-40-8)

Guidance literature:

N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl]methanesulfonamide; With potassium carbonate; sodium iodide; In dimethyl sulfoxide; for 0.166667h; Inert atmosphere; microwave tube;

Ethyl 4-bromobutyrate; In dimethyl sulfoxide; at 20 ℃; for 72h; Inert atmosphere; microwave tube; sealed tube;

Reference yield:

1-(4-fluorophenyl)ethanone (403-42-9) → methyl 4-{[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl](methylsulfonyl)amino}butanoate (1383851-40-8)

Guidance literature:

Multi-step reaction with 16 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

12.1: dipyridinium dichromate / dichloromethane / 18 h / 20 °C

13.1: dichloromethane / 4.5 h / 20 °C / Inert atmosphere

13.2: 136 h / 20 °C / Cooling with ice; Inert atmosphere; Molecular sieve

14.1: [bis(acetoxy)iodo]benzene / dimethyl sulfoxide / 2.5 h / 20 °C / Inert atmosphere

15.1: trifluoroacetic acid / dichloromethane / 3.58 h / 10 - 20 °C / Inert atmosphere

16.1: potassium carbonate; sodium iodide / dimethyl sulfoxide / 0.17 h / Inert atmosphere; microwave tube

16.2: 72 h / 20 °C / Inert atmosphere; microwave tube; sealed tube

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

Reference yield:

ethyl 3-(4'-fluorophenyl)-3-oxopropionate (1999-00-4) → methyl 4-{[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl](methylsulfonyl)amino}butanoate (1383851-40-8)

Guidance literature:

Multi-step reaction with 15 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

11.1: dipyridinium dichromate / dichloromethane / 18 h / 20 °C

12.1: dichloromethane / 4.5 h / 20 °C / Inert atmosphere

12.2: 136 h / 20 °C / Cooling with ice; Inert atmosphere; Molecular sieve

13.1: [bis(acetoxy)iodo]benzene / dimethyl sulfoxide / 2.5 h / 20 °C / Inert atmosphere

14.1: trifluoroacetic acid / dichloromethane / 3.58 h / 10 - 20 °C / Inert atmosphere

15.1: potassium carbonate; sodium iodide / dimethyl sulfoxide / 0.17 h / Inert atmosphere; microwave tube

15.2: 72 h / 20 °C / Inert atmosphere; microwave tube; sealed tube

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

upstream raw materials:

Ethyl 4-bromobutyrate

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

1-(4-fluorophenyl)ethanone

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

Downstream raw materials:

tert-butyl 2-(4-(N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)benzofuran-6-yl)methylsulfonamido)butanoyl)hydrazinecarboxylate

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

N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)-1-benzofuran-6-yl]-N-[3-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)propyl]methanesulfonamide

N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)benzofuran-6-yl)-N-(4-hydrazinyl-4-oxobutyl)methanesulfonamide

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