(S)-3-[4-ethyl-1-(toluene-4-sulfonyl)-1H-indol-7-yl]-butan-1-ol

Base Information

Chemical Name:(S)-3-[4-ethyl-1-(toluene-4-sulfonyl)-1H-indol-7-yl]-butan-1-ol
CAS No.:1365987-72-9
Molecular Formula:C₂₁H₂₅NO₃S
Molecular Weight:371.5
Hs Code.:

Synonyms:(S)-3-[4-ethyl-1-(toluene-4-sulfonyl)-1H-indol-7-yl]-butan-1-ol

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Chemical Property of (S)-3-[4-ethyl-1-(toluene-4-sulfonyl)-1H-indol-7-yl]-butan-1-ol

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Technology Process of (S)-3-[4-ethyl-1-(toluene-4-sulfonyl)-1H-indol-7-yl]-butan-1-ol

There total 5 articles about (S)-3-[4-ethyl-1-(toluene-4-sulfonyl)-1H-indol-7-yl]-butan-1-ol 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: 92.0%

: 1365987-68-3
(S)-4-ethyl-7-(2-but-3-enyl)-1-(toluene-4-sulfonyl)-1H-indole

: 1365987-72-9
(S)-3-[4-ethyl-1-(toluene-4-sulfonyl)-1H-indol-7-yl]-butan-1-ol

Guidance literature:: (S)-4-ethyl-7-(2-but-3-enyl)-1-(toluene-4-sulfonyl)-1H-indole; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 0 - 20 ℃; for 1.5h; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1021/ja3004733

Reference yield:

: 1365987-29-6
4-ethyl-7-vinyl-1H-indole

: 1365987-72-9
(S)-3-[4-ethyl-1-(toluene-4-sulfonyl)-1H-indol-7-yl]-butan-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: bi(allylnickel bromide); (R)-2,2'-binaphthoyl-benzyl-(S)-[1-(1-naphthylethyl)]aminoylphosphine; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / dichloromethane / 3.03 h / -78 °C / 760.05 Torr

2.1: 18-crown-6 ether; potassium hydride / 1,2-dimethoxyethane / 0.5 h / 0 - 20 °C / Inert atmosphere

2.2: 14 h / 0 - 20 °C / Inert atmosphere

3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere

3.2: 0.5 h / 0 - 20 °C / Inert atmosphere

With 18-crown-6 ether; bi(allylnickel bromide); (R)-2,2'-binaphthoyl-benzyl-(S)-[1-(1-naphthylethyl)]aminoylphosphine; potassium hydride; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/ja3004733

Reference yield:

: 1585-07-5
1-bromo-4-ethylbenzene

: 1365987-72-9
(S)-3-[4-ethyl-1-(toluene-4-sulfonyl)-1H-indol-7-yl]-butan-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: sulfuric acid; nitric acid / 0.67 h / 20 °C / Cooling with ice

2.1: tetrahydrofuran / 1.42 h / -50 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 2 h / Inert atmosphere; Reflux

4.1: bi(allylnickel bromide); sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; N,N-bis-[(S)-1-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine / dichloromethane / 3.03 h / -78 °C / 760.05 Torr

5.1: 18-crown-6 ether; potassium hydride / 1,2-dimethoxyethane / 0.5 h / 0 - 20 °C / Inert atmosphere

5.2: 14 h / 0 - 20 °C / Inert atmosphere

6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere

6.2: 0.5 h / 0 - 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 18-crown-6 ether; bi(allylnickel bromide); sulfuric acid; nitric acid; potassium hydride; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; 9-bora-bicyclo[3.3.1]nonane; N,N-bis-[(S)-1-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; toluene; 3.1: Stille coupling;
DOI:10.1021/ja3004733