3-[(R)-1-(4-chlorophenyl)-2-fluoro-2,2-bis(phenylsulfonyl)ethyl]-2-phenyl-1H-indole

Base Information

• Chemical Name: 3-[(R)-1-(4-chlorophenyl)-2-fluoro-2,2-bis(phenylsulfonyl)ethyl]-2-phenyl-1H-indole
• CAS No.: 1443532-38-4
• Molecular Formula: C₃₄H₂₅ClFNO₄S₂
• Molecular Weight: 630.16
• Mol file: 1443532-38-4.mol

Synonyms:

Chemical Property of 3-[(R)-1-(4-chlorophenyl)-2-fluoro-2,2-bis(phenylsulfonyl)ethyl]-2-phenyl-1H-indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(R)-1-(4-chlorophenyl)-2-fluoro-2,2-bis(phenylsulfonyl)ethyl]-2-phenyl-1H-indole

There total 3 articles about 3-[(R)-1-(4-chlorophenyl)-2-fluoro-2,2-bis(phenylsulfonyl)ethyl]-2-phenyl-1H-indole 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:

1-fluoro-1,1-bis(phenylsulfonyl)methane (910650-82-7) + 3-[(4-chlorophenyl)(tosyl)methyl]-2-phenyl-1H-indole (1443382-80-6) → 3-[(R)-1-(4-chlorophenyl)-2-fluoro-2,2-bis(phenylsulfonyl)ethyl]-2-phenyl-1H-indole (1443532-38-4) + 3-[(S)-1-(4-chlorophenyl)-2-fluoro-2,2-bis(phenylsulfonyl)ethyl]-2-phenyl-1H-indole

Guidance literature:

With C₃₄H₄₅N₂O⁽¹⁺⁾*Br^(1-); caesium carbonate; In toluene; at -10 ℃; for 72h; Overall yield = 78 %; Overall yield = 49.2 mg; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol4013102

Reference yield:

4-chlorobenzaldehyde (104-88-1) → 3-[(R)-1-(4-chlorophenyl)-2-fluoro-2,2-bis(phenylsulfonyl)ethyl]-2-phenyl-1H-indole (1443532-38-4) + 3-[(S)-1-(4-chlorophenyl)-2-fluoro-2,2-bis(phenylsulfonyl)ethyl]-2-phenyl-1H-indole

Guidance literature:

Multi-step reaction with 3 steps

1: formic acid / tetrahydrofuran; water / 20 °C / Inert atmosphere

2: indium(III) bromide / dichloromethane / 20 °C / Inert atmosphere

3: C₃₄H₄₅N₂O⁽¹⁺⁾*Br^(1-); caesium carbonate / toluene / 72 h / -10 °C / Inert atmosphere

With formic acid; indium(III) bromide; C₃₄H₄₅N₂O⁽¹⁺⁾*Br^(1-); caesium carbonate; In tetrahydrofuran; dichloromethane; water; toluene; 2: |Friedel-Crafts Alkylation;

DOI:10.1021/ol4013102

Reference yield:

ethyl N-[(4-chlorophenyl)(tosyl)methyl]carbamate (1190879-95-8) → 3-[(R)-1-(4-chlorophenyl)-2-fluoro-2,2-bis(phenylsulfonyl)ethyl]-2-phenyl-1H-indole (1443532-38-4) + 3-[(S)-1-(4-chlorophenyl)-2-fluoro-2,2-bis(phenylsulfonyl)ethyl]-2-phenyl-1H-indole

Guidance literature:

Multi-step reaction with 2 steps

1: indium(III) bromide / dichloromethane / 20 °C / Inert atmosphere

2: C₃₄H₄₅N₂O⁽¹⁺⁾*Br^(1-); caesium carbonate / toluene / 72 h / -10 °C / Inert atmosphere

With indium(III) bromide; C₃₄H₄₅N₂O⁽¹⁺⁾*Br^(1-); caesium carbonate; In dichloromethane; toluene; 1: |Friedel-Crafts Alkylation;

DOI:10.1021/ol4013102

upstream raw materials:

1-fluoro-1,1-bis(phenylsulfonyl)methane

3-[(4-chlorophenyl)(tosyl)methyl]-2-phenyl-1H-indole

ethyl N-[(4-chlorophenyl)(tosyl)methyl]carbamate

4-chlorobenzaldehyde