ethyl 2-azido-5-methyl-3-[1-(4-toluenesulfonyl)indol-3-yl]hex-4-enoate

Base Information

Chemical Name:ethyl 2-azido-5-methyl-3-[1-(4-toluenesulfonyl)indol-3-yl]hex-4-enoate
CAS No.:1339939-38-6
Molecular Formula:C₂₄H₂₆N₄O₄S
Molecular Weight:466.561
Hs Code.:

Synonyms:ethyl 2-azido-5-methyl-3-[1-(4-toluenesulfonyl)indol-3-yl]hex-4-enoate

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Chemical Property of ethyl 2-azido-5-methyl-3-[1-(4-toluenesulfonyl)indol-3-yl]hex-4-enoate

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Technology Process of ethyl 2-azido-5-methyl-3-[1-(4-toluenesulfonyl)indol-3-yl]hex-4-enoate

There total 5 articles about ethyl 2-azido-5-methyl-3-[1-(4-toluenesulfonyl)indol-3-yl]hex-4-enoate 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: 63.0%

: 1339939-33-1
ethyl 5-methyl-3-[1-(4-toluenesulfonyl)indol-3-yl]hex-4-enoate

: 1339939-38-6
ethyl 2-azido-5-methyl-3-[1-(4-toluenesulfonyl)indol-3-yl]hex-4-enoate

Guidance literature:: ethyl 5-methyl-3-[1-(4-toluenesulfonyl)indol-3-yl]hex-4-enoate; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h; Inert atmosphere;

With 2,4,6-Triisopropylbenzenesulfonyl azide; In tetrahydrofuran; toluene; at -78 ℃; for 0.0833333h; Inert atmosphere;

With acetic acid; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1016/j.tet.2011.08.094

Reference yield:

: 487-89-8,1228547-52-1
Indole-3-carboxaldehyde

: 1339939-38-6
ethyl 2-azido-5-methyl-3-[1-(4-toluenesulfonyl)indol-3-yl]hex-4-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap; triethylamine / 4 h / 20 °C

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.25 h / 20 °C / Inert atmosphere

2.2: 2 h / 20 °C / Inert atmosphere

3.1: copper(I) thiophenolate / tetrahydrofuran / 1 h / -40 - 0 °C / Inert atmosphere

3.2: 2 h / -40 - 20 °C / Inert atmosphere

4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

4.2: 0.08 h / -78 °C / Inert atmosphere

4.3: 0.5 h / -78 - 20 °C / Inert atmosphere

With dmap; copper(I) thiophenolate; potassium hexamethylsilazane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; In tetrahydrofuran; toluene; acetonitrile; 2.2: Horner-Wadsworth-Emmons olefination / 3.2: Michael condensation;
DOI:10.1016/j.tet.2011.08.094

Reference yield:

: 50562-79-3
1-(4-tolylsulfonyl)indole-3-carboxaldehyde

: 1339939-38-6
ethyl 2-azido-5-methyl-3-[1-(4-toluenesulfonyl)indol-3-yl]hex-4-enoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.25 h / 20 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: copper(I) thiophenolate / tetrahydrofuran / 1 h / -40 - 0 °C / Inert atmosphere

2.2: 2 h / -40 - 20 °C / Inert atmosphere

3.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

3.2: 0.08 h / -78 °C / Inert atmosphere

3.3: 0.5 h / -78 - 20 °C / Inert atmosphere

With copper(I) thiophenolate; potassium hexamethylsilazane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; toluene; acetonitrile; 1.2: Horner-Wadsworth-Emmons olefination / 2.2: Michael condensation;
DOI:10.1016/j.tet.2011.08.094