ethyl 4-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-4-(2-(ethoxycarbonyl)allyl)imidazol-5-yl)benzoate

Base Information

• Chemical Name: ethyl 4-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-4-(2-(ethoxycarbonyl)allyl)imidazol-5-yl)benzoate
• CAS No.: 1609648-75-0
• Molecular Formula: C₂₆H₃₉N₃O₆SSi
• Molecular Weight: 549.764

Synonyms:ethyl 4-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-4-(2-(ethoxycarbonyl)allyl)imidazol-5-yl)benzoate

Chemical Property of ethyl 4-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-4-(2-(ethoxycarbonyl)allyl)imidazol-5-yl)benzoate

Chemical Property:

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Technology Process of ethyl 4-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-4-(2-(ethoxycarbonyl)allyl)imidazol-5-yl)benzoate

There total 5 articles about ethyl 4-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-4-(2-(ethoxycarbonyl)allyl)imidazol-5-yl)benzoate 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: 71.0%

4-iodobenzoic acid ethyl ester (51934-41-9) + ethyl 2-((2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-5-((4-methoxy-3,5-dimethylphenyl)sulfinyl)imidazol-4-yl)methyl)acrylate (1609648-67-0) → ethyl 4-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-4-(2-(ethoxycarbonyl)allyl)imidazol-5-yl)benzoate (1609648-75-0)

Guidance literature:

ethyl 2-((2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-5-((4-methoxy-3,5-dimethylphenyl)sulfinyl)imidazol-4-yl)methyl)acrylate; With TurboGrignard; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere; Schlenk technique;

With zinc(II) chloride; In tetrahydrofuran; at -30 ℃; for 0.25h; Inert atmosphere;

4-iodobenzoic acid ethyl ester; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 50 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.201309217

Reference yield:

2-(tert-butyldimethylsilyl)-5-((4-methoxy-3,5-dimethylphenyl)sulfinyl)N,N-dimethylimidazole-1-sulfonamide (1609648-50-1) → ethyl 4-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-4-(2-(ethoxycarbonyl)allyl)imidazol-5-yl)benzoate (1609648-75-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex / tetrahydrofuran / 1 h / -30 °C / Inert atmosphere; Schlenk technique

1.2: 0.25 h / -30 °C / Inert atmosphere

1.3: 12 h / 50 °C / Inert atmosphere

2.1: TurboGrignard / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere; Schlenk technique

2.2: 0.25 h / -30 °C / Inert atmosphere

2.3: 2 h / 50 °C / Inert atmosphere

With TurboGrignard; 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex; In tetrahydrofuran; 1.3: |Negishi Coupling / 2.3: |Negishi Coupling;

DOI:10.1002/anie.201309217

Reference yield:

N,N-dimethyl-1H-imidazole-1-sulfonamide (78162-58-0) → ethyl 4-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-4-(2-(ethoxycarbonyl)allyl)imidazol-5-yl)benzoate (1609648-75-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 - 25 °C / Inert atmosphere

2.1: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere; Schlenk technique

2.2: 4 h / -20 - 20 °C / Inert atmosphere; Schlenk technique

3.1: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex / tetrahydrofuran / 1 h / -30 °C / Inert atmosphere; Schlenk technique

3.2: 0.25 h / -30 °C / Inert atmosphere

3.3: 12 h / 50 °C / Inert atmosphere

4.1: TurboGrignard / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere; Schlenk technique

4.2: 0.25 h / -30 °C / Inert atmosphere

4.3: 2 h / 50 °C / Inert atmosphere

With TurboGrignard; n-butyllithium; 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex; In tetrahydrofuran; 3.3: |Negishi Coupling / 4.3: |Negishi Coupling;

DOI:10.1002/anie.201309217

upstream raw materials:

2-(tert-butyldimethylsilyl)-5-((4-methoxy-3,5-dimethylphenyl)sulfinyl)N,N-dimethylimidazole-1-sulfonamide

N,N-dimethyl-1H-imidazole-1-sulfonamide

2-tert-butyldimethylsilyl-N,N-dimethylimidazole-1-sulfonamide

tert-butyldimethylsilyl chloride

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