Methanesulfonic acid, trifluoro-, 3-[2,5-dihydro-1-methyl-2,5-dioxo-4-[1-(phenylsulfonyl)-1H-indol-3-yl]-1 H-pyrrol-3-yl]-2-naphthalenyl ester

Base Information

• Chemical Name: Methanesulfonic acid, trifluoro-, 3-[2,5-dihydro-1-methyl-2,5-dioxo-4-[1-(phenylsulfonyl)-1H-indol-3-yl]-1 H-pyrrol-3-yl]-2-naphthalenyl ester
• CAS No.: 386235-60-5
• Molecular Formula: C30H19F3N2O7S2
• Molecular Weight: 640.617
• Mol file: 386235-60-5.mol

Synonyms:

Chemical Property of Methanesulfonic acid, trifluoro-, 3-[2,5-dihydro-1-methyl-2,5-dioxo-4-[1-(phenylsulfonyl)-1H-indol-3-yl]-1 H-pyrrol-3-yl]-2-naphthalenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid, trifluoro-, 3-[2,5-dihydro-1-methyl-2,5-dioxo-4-[1-(phenylsulfonyl)-1H-indol-3-yl]-1 H-pyrrol-3-yl]-2-naphthalenyl ester

There total 9 articles about Methanesulfonic acid, trifluoro-, 3-[2,5-dihydro-1-methyl-2,5-dioxo-4-[1-(phenylsulfonyl)-1H-indol-3-yl]-1 H-pyrrol-3-yl]-2-naphthalenyl ester 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: 98.0%

trifluoromethylsulfonic anhydride (358-23-6) + 3-(1-benzenesulfonyl-1H-indol-3-yl)-4-(3-hydroxy-naphthalen-2-yl)-1-methyl-pyrrole-2,5-dione (386235-58-1) → trifluoromethanesulfonic acid 3-[4-(1-benzenesulfonyl-1H-indol-3-yl)-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]naphthalen-2-yl ester (386235-60-5)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 3h;

DOI:10.1016/S0040-4039(01)01308-9

Reference yield:

3-bromo-4-(1H-indol-3-yl)-1-methyl-1H-pyrrole-2,5-dione (119139-14-9) → trifluoromethanesulfonic acid 3-[4-(1-benzenesulfonyl-1H-indol-3-yl)-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]naphthalen-2-yl ester (386235-60-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 55 percent / Pd(OAc)2; aq. K₂CO₃ / dioxane / 2 h / 100 °C

2.1: NaH / tetrahydrofuran / 0 °C

2.2: 96 percent / tetrahydrofuran / 20 °C

3.1: 98 percent / BBr₃ / CH₂Cl₂ / 1 h / 0 °C

4.1: 98 percent / NEt₃ / CH₂Cl₂ / 5 h / 0 - 20 °C

With palladium diacetate; boron tribromide; sodium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 1.1: Suzuki coupling reaction;

DOI:10.1021/jm049213f

Reference yield:

3-(1-benzenesulfonyl-1H-indol-3-yl)-4-bromo-1-methyl-pyrrole-2,5-dione (386235-52-5) → trifluoromethanesulfonic acid 3-[4-(1-benzenesulfonyl-1H-indol-3-yl)-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]naphthalen-2-yl ester (386235-60-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / Pd(OAc)2; aq. K₂CO₃ / dioxane / 2 h / 100 °C

2: 98 percent / BBr₃ / CH₂Cl₂ / 1 h / 0 °C

3: 98 percent / NEt₃ / CH₂Cl₂ / 5 h / 0 - 20 °C

With palladium diacetate; boron tribromide; potassium carbonate; triethylamine; In 1,4-dioxane; dichloromethane; 1: Suzuki coupling reaction;

DOI:10.1021/jm049213f

upstream raw materials:

trifluoromethylsulfonic anhydride

3-(1-benzenesulfonyl-1H-indol-3-yl)-4-(3-hydroxy-naphthalen-2-yl)-1-methyl-pyrrole-2,5-dione

3-bromo-4-(1H-indol-3-yl)-1-methyl-1H-pyrrole-2,5-dione

tert-butyl 3-(4-bromo-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole-1-carboxylate

Downstream raw materials:

6-methyl-14-benzenesulfonyl-naphtho[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H,14H)-dione