(+)-N-[(E)-3-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-2-propenoyl]bornane-10,2-sultam

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Chemical Name:(+)-N-[(E)-3-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-2-propenoyl]bornane-10,2-sultam
CAS No.:468717-85-3
Molecular Formula:C₂₉H₂₉N₃O₅S₂
Molecular Weight:563.698
Hs Code.:

Synonyms:(+)-N-[(E)-3-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-2-propenoyl]bornane-10,2-sultam

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Chemical Property of (+)-N-[(E)-3-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-2-propenoyl]bornane-10,2-sultam

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Technology Process of (+)-N-[(E)-3-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-2-propenoyl]bornane-10,2-sultam

There total 3 articles about (+)-N-[(E)-3-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-2-propenoyl]bornane-10,2-sultam 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: 58.0%

: 468717-73-9
3-formyl-1-(toluene-4-sulfonyl)-1H-indole-5-carbonitrile

: 263768-73-6
(2S)-N-(2-(diethylphosphonyl)-acetyl)-camphor-10,2-sultam

: 468717-85-3
(+)-N-[(E)-3-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-2-propenoyl]bornane-10,2-sultam

Guidance literature:: (2S)-N-(2-(diethylphosphonyl)-acetyl)-camphor-10,2-sultam; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h;

3-formyl-1-(toluene-4-sulfonyl)-1H-indole-5-carbonitrile; In tetrahydrofuran; at 20 ℃; for 24h;
DOI:10.1021/jm0503291

Reference yield:

: 15861-24-2,142396-06-3
1H-indole-5-carbonitrile

: 468717-85-3
(+)-N-[(E)-3-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-2-propenoyl]bornane-10,2-sultam

Guidance literature:: Multi-step reaction with 3 steps

1.1: POCl₃ / 0.5 h / 10 - 20 °C

1.2: 75 percent / dimethylformamide / 2 h / 20 °C

2.1: 65 percent / triethylamine / CH₂Cl₂ / 24 h / 20 °C

3.1: NaH / tetrahydrofuran / 1 h / 20 °C

3.2: 58 percent / tetrahydrofuran / 24 h / 20 °C

With sodium hydride; triethylamine; trichlorophosphate; In tetrahydrofuran; dichloromethane; 1.2: Vilsmeier-Haack formylation / 3.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jm0503291

Reference yield:

: 17380-18-6
3-formyl-1H-indole-5-carbonitrile

: 468717-85-3
(+)-N-[(E)-3-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]-2-propenoyl]bornane-10,2-sultam

Guidance literature:: Multi-step reaction with 2 steps

1.1: 65 percent / triethylamine / CH₂Cl₂ / 24 h / 20 °C

2.1: NaH / tetrahydrofuran / 1 h / 20 °C

2.2: 58 percent / tetrahydrofuran / 24 h / 20 °C

With sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jm0503291