(1S,2S)-trans-2-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]cyclopropanecarboxaldehyde

Base Information

Chemical Name:(1S,2S)-trans-2-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]cyclopropanecarboxaldehyde
CAS No.:468718-47-0
Molecular Formula:C₂₀H₁₆N₂O₃S
Molecular Weight:364.425
Hs Code.:

Synonyms:(1S,2S)-trans-2-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]cyclopropanecarboxaldehyde

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Chemical Property of (1S,2S)-trans-2-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]cyclopropanecarboxaldehyde

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Technology Process of (1S,2S)-trans-2-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]cyclopropanecarboxaldehyde

There total 10 articles about (1S,2S)-trans-2-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]cyclopropanecarboxaldehyde 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: 94.0%

: 468717-34-2
3-((1S,2S)-2-hydroxymethylcyclopropyl)-1-(toluene-4-sulfonyl)-1H-indole-5-carbonitrile

: 468718-47-0
(1S,2S)-trans-2-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]cyclopropanecarboxaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -70 - 20 ℃;
DOI:10.1021/ol050790n

Reference yield:

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

: 468718-47-0
(1S,2S)-trans-2-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]cyclopropanecarboxaldehyde

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 58 percent / tetrahydrofuran / 24 h / 20 °C

2.1: 46 percent / palladium acetate / CH₂Cl₂; diethyl ether / 0.33 h / -10 - -5 °C

3.1: 81 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / -40 °C

4.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

With lithium aluminium tetrahydride; oxalyl dichloride; palladium diacetate; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1.2: Horner-Wadsworth-Emmons olefination / 4.1: Swern oxidation;
DOI:10.1021/jm0503291

Reference yield:

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

: 468718-47-0
(1S,2S)-trans-2-[5-cyano-1-(4-toluenesulfonyl)-1H-indol-3-yl]cyclopropanecarboxaldehyde

Guidance literature:: Multi-step reaction with 6 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

4.1: 46 percent / palladium acetate / CH₂Cl₂; diethyl ether / 0.33 h / -10 - -5 °C

5.1: 81 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / -40 °C

6.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

With lithium aluminium tetrahydride; oxalyl dichloride; palladium diacetate; sodium hydride; dimethyl sulfoxide; triethylamine; trichlorophosphate; In tetrahydrofuran; diethyl ether; dichloromethane; 1.2: Vilsmeier-Haack formylation / 3.2: Horner-Wadsworth-Emmons olefination / 6.1: Swern oxidation;
DOI:10.1021/jm0503291