ethyl 3-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-5-((4-methoxy-3,5-dimethylphenyl)sulfinyl)imidazol-4-yl)prop-2-ynoate

Base Information

Chemical Name:ethyl 3-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-5-((4-methoxy-3,5-dimethylphenyl)sulfinyl)imidazol-4-yl)prop-2-ynoate
CAS No.:1609648-71-6
Molecular Formula:C₂₅H₃₇N₃O₆S₂Si
Molecular Weight:567.803
Hs Code.:

Synonyms:ethyl 3-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-5-((4-methoxy-3,5-dimethylphenyl)sulfinyl)imidazol-4-yl)prop-2-ynoate

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Chemical Property of ethyl 3-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-5-((4-methoxy-3,5-dimethylphenyl)sulfinyl)imidazol-4-yl)prop-2-ynoate

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Technology Process of ethyl 3-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-5-((4-methoxy-3,5-dimethylphenyl)sulfinyl)imidazol-4-yl)prop-2-ynoate

There total 4 articles about ethyl 3-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-5-((4-methoxy-3,5-dimethylphenyl)sulfinyl)imidazol-4-yl)prop-2-ynoate 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: 53.0%

: 1609648-50-1
2-(tert-butyldimethylsilyl)-5-((4-methoxy-3,5-dimethylphenyl)sulfinyl)N,N-dimethylimidazole-1-sulfonamide

: 41658-03-1
ethyl 3-bromoprop-2-ynoate

: 1609648-71-6
ethyl 3-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-5-((4-methoxy-3,5-dimethylphenyl)sulfinyl)imidazol-4-yl)prop-2-ynoate

Guidance literature:: 2-(tert-butyldimethylsilyl)-5-((4-methoxy-3,5-dimethylphenyl)sulfinyl)N,N-dimethylimidazole-1-sulfonamide; With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex; In tetrahydrofuran; at -30 ℃; for 1h; Inert atmosphere; Schlenk technique;

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

ethyl 3-bromoprop-2-ynoate; With copper(I) cyanide di(lithium chloride); In tetrahydrofuran; at 50 ℃; for 12h; Inert atmosphere;
DOI:10.1002/anie.201309217

Reference yield:

: 78162-58-0
N,N-dimethyl-1H-imidazole-1-sulfonamide

: 1609648-71-6
ethyl 3-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-5-((4-methoxy-3,5-dimethylphenyl)sulfinyl)imidazol-4-yl)prop-2-ynoate

Guidance literature:: Multi-step reaction with 3 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

With n-butyllithium; 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex; In tetrahydrofuran; 3.3: |Negishi Coupling;
DOI:10.1002/anie.201309217

Reference yield:

: 129378-52-5
2-tert-butyldimethylsilyl-N,N-dimethylimidazole-1-sulfonamide

: 1609648-71-6
ethyl 3-(2-(tert-butyldimethylsilyl)-1-(N,N-dimethylsulfamoyl)-5-((4-methoxy-3,5-dimethylphenyl)sulfinyl)imidazol-4-yl)prop-2-ynoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere; Schlenk technique

1.2: 4 h / -20 - 20 °C / Inert atmosphere; Schlenk technique

2.1: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex / tetrahydrofuran / 1 h / -30 °C / Inert atmosphere; Schlenk technique

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

2.3: 12 h / 50 °C / Inert atmosphere

With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex; In tetrahydrofuran; 2.3: |Negishi Coupling;
DOI:10.1002/anie.201309217