(1S,8S,11S)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-diene-7,10-dione

Base Information

• Chemical Name: (1S,8S,11S)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-diene-7,10-dione
• CAS No.: 852380-97-3
• Molecular Formula: C₃₉H₄₃BrN₄O₇SSi
• Molecular Weight: 819.849
• Mol file: 852380-97-3.mol

Synonyms:(1S,8S,11S)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-diene-7,10-dione

Chemical Property of (1S,8S,11S)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-diene-7,10-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,8S,11S)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-diene-7,10-dione

There total 17 articles about (1S,8S,11S)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-diene-7,10-dione 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: 89.0%

(1S,8S,11S)-8-Methoxy-11-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene-7,10-dione (852380-63-3) + 5-bromo-3-methoxy-2-(N-tosyl-6-bromoindol-3-yl)pyrazine (476623-17-3) → (1S,8S,11S)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene-7,10-dione (852380-97-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In methanol; benzene; at 50 ℃; for 72h;

DOI:10.1021/ja050586v

Reference yield:

(1R,8S,10R)-10-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-11-methylene-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.02,6]dodeca-2(6),3-dien-7-one (852380-53-1) → (1S,8S,11S)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene-7,10-dione (852380-97-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaH / tetrahydrofuran / 0.02 h / 23 °C

1.2: 28.2 mg / tetrahydrofuran / 1.5 h

2.1: 95 percent / TBAF / tetrahydrofuran / 4 h / 23 °C

3.1: 98 percent / Rh(nbd)(dppb)BF₄; H₂ / CH₂Cl₂ / 3 h / 23 °C / 760 Torr

4.1: 98 percent / N-bromosuccinimide / tetrahydrofuran / 0.25 h / Heating

5.1: 74 percent / n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

6.1: 89 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾; aq. Na₂CO₃ / benzene; methanol / 72 h / 50 °C

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium carbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene; 6.1: Suzuki coupling;

DOI:10.1021/ja050586v

Reference yield:

(1R,8S,10R)-10-Hydroxy-8-methoxy-11-methylene-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.02,6]dodeca-2(6),3-dien-7-one (852380-61-1) → (1S,8S,11S)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene-7,10-dione (852380-97-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / Rh(nbd)(dppb)BF₄; H₂ / CH₂Cl₂ / 3 h / 23 °C / 760 Torr

2: 98 percent / N-bromosuccinimide / tetrahydrofuran / 0.25 h / Heating

3: 74 percent / n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

4: 89 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾; aq. Na₂CO₃ / benzene; methanol / 72 h / 50 °C

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; hydrogen; sodium carbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene; 4: Suzuki coupling;

DOI:10.1021/ja050586v

upstream raw materials:

(1S,8S,11S)-8-Methoxy-11-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-diene-7,10-dione

5-bromo-3-methoxy-2-(N-tosyl-6-bromoindol-3-yl)pyrazine

(1S,8S,11S)-8-Methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-diene-7,10-dione

(1R,8S,10R)-10-Hydroxy-8-methoxy-11-methylene-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-dien-7-one