trans-3-[7-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide

Base Information

• Chemical Name: trans-3-[7-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide
• CAS No.: 863407-43-6
• Molecular Formula: C₂₁H₁₉N₃O₄S
• Molecular Weight: 409.466
• Mol file: 863407-43-6.mol

Synonyms:trans-3-[7-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide

Chemical Property of trans-3-[7-cyano-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-[7-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide

There total 3 articles about trans-3-[7-cyano-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%

3-formyl-1-(4-toluenesulfonyl)-1H-indole-7-carbonitrile (863407-38-9) + diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate (124931-12-0) → trans-3-[7-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide (863407-43-6)

Guidance literature:

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

3-formyl-1-(4-toluenesulfonyl)-1H-indole-7-carbonitrile; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/jm0503291

Reference yield:

3-formyl-7-cyano-1H-indole (467451-63-4) → trans-3-[7-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide (863407-43-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / CH₂Cl₂ / 20 °C

2.1: NaH / tetrahydrofuran / 20 °C

2.2: 88 percent / tetrahydrofuran / 0 °C

With sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; 2.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/jm0503291

Reference yield:

1H-indole-7-carbonitrile (96631-87-7) → trans-3-[7-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-N-methoxy-N-methylacrylamide (863407-43-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: POCl₃ / 10 - 20 °C

1.2: dimethylformamide / 20 °C

2.1: triethylamine / CH₂Cl₂ / 20 °C

3.1: NaH / tetrahydrofuran / 20 °C

3.2: 88 percent / tetrahydrofuran / 0 °C

With sodium hydride; triethylamine; trichlorophosphate; In tetrahydrofuran; dichloromethane; 1.2: Vilsmeier-Haack formylation / 3.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/jm0503291

upstream raw materials:

3-formyl-1-(4-toluenesulfonyl)-1H-indole-7-carbonitrile

diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate

3-formyl-7-cyano-1H-indole

1H-indole-7-carbonitrile