trans-3-[5-fluoro-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide

Base Information

• Chemical Name: trans-3-[5-fluoro-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide
• CAS No.: 468717-78-4
• Molecular Formula: C₂₀H₁₉FN₂O₄S
• Molecular Weight: 402.446
• Mol file: 468717-78-4.mol

Synonyms:trans-3-[5-fluoro-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide

Chemical Property of trans-3-[5-fluoro-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-3-[5-fluoro-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide

There total 1 articles about trans-3-[5-fluoro-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide 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: 88.0%

diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate (124931-12-0) + 5-fluoro-1-(p-tolylsulfonyl)indole-3-carboxaldehyde (217489-00-4) → trans-3-[5-fluoro-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide (468717-78-4)

Guidance literature:

diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate; With sodium hydride; In tetrahydrofuran; at 20 ℃;

5-fluoro-1-(p-tolylsulfonyl)indole-3-carboxaldehyde; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/jm0503291

Reference yield: 99.0%

trans-3-[5-fluoro-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide (468717-78-4) + diazomethane (186581-53-3,908094-01-9,334-88-3) → trans-2-[5-fluoro-1-(4-toluenesulfonyl)-1H-indol-3-yl]cycloprop-1-yl-N-methoxy-N-methylcarboxamide

Guidance literature:

With palladium diacetate; In diethyl ether; dichloromethane; at 0 ℃;

DOI:10.1021/jm0503291

Reference yield:

trans-3-[5-fluoro-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide (468717-78-4) → trans-2-[5-fluoro-1-(4-toluenesulfonyl)-1H-indol-3-yl]cyclopropanecarboxaldehyde

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / palladium acetate / CH₂Cl₂; diethyl ether / 0 °C

2: 76 percent / LiAlH₄ / tetrahydrofuran / -40 °C

With lithium aluminium tetrahydride; palladium diacetate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jm0503291

upstream raw materials:

diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate

5-fluoro-1-(p-tolylsulfonyl)indole-3-carboxaldehyde