1-[6-chloro-2-(4-nitrobenzenesulfonyl)-1-vinyl-1,2,3,4-tetrahydro-β-carbolin-9-yl]-propenone

Base Information

Chemical Name:1-[6-chloro-2-(4-nitrobenzenesulfonyl)-1-vinyl-1,2,3,4-tetrahydro-β-carbolin-9-yl]-propenone
CAS No.:859163-73-8
Molecular Formula:C₂₂H₁₈ClN₃O₅S
Molecular Weight:471.921
Hs Code.:

Synonyms:1-[6-chloro-2-(4-nitrobenzenesulfonyl)-1-vinyl-1,2,3,4-tetrahydro-β-carbolin-9-yl]-propenone

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Chemical Property of 1-[6-chloro-2-(4-nitrobenzenesulfonyl)-1-vinyl-1,2,3,4-tetrahydro-β-carbolin-9-yl]-propenone

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Technology Process of 1-[6-chloro-2-(4-nitrobenzenesulfonyl)-1-vinyl-1,2,3,4-tetrahydro-β-carbolin-9-yl]-propenone

There total 6 articles about 1-[6-chloro-2-(4-nitrobenzenesulfonyl)-1-vinyl-1,2,3,4-tetrahydro-β-carbolin-9-yl]-propenone 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: 41.0%

: 859163-72-7
6-chloro-2-(4-nitrobenzenesulfonyl)-1-vinyl-2,3,4,9-tetrahydro-1H-β-carboline

: 814-68-6,25189-84-8
acryloyl chloride

: 859163-73-8
1-[6-chloro-2-(4-nitrobenzenesulfonyl)-1-vinyl-1,2,3,4-tetrahydro-β-carbolin-9-yl]-propenone

Guidance literature:: 6-chloro-2-(4-nitrobenzenesulfonyl)-1-vinyl-2,3,4,9-tetrahydro-1H-β-carboline; With potassium hexamethylsilazane; In tetrahydrofuran; at 20 ℃; for 1.5h;

acryloyl chloride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/jo050503t

Reference yield:

: 98993-95-4
5-chloro-3-(2-nitrovinyl)indole

: 859163-73-8
1-[6-chloro-2-(4-nitrobenzenesulfonyl)-1-vinyl-1,2,3,4-tetrahydro-β-carbolin-9-yl]-propenone

Guidance literature:: Multi-step reaction with 5 steps

1.1: 99 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

2.1: 75 percent / Et₃N / CH₂Cl₂ / 6 h / 20 °C

3.1: 83 percent / Et₃N / Pd(OAc)2 / acetonitrile / 2 h / 20 °C

4.1: 94 percent / Sn(OTf)2 / CH₂Cl₂ / 2 h / 0 °C

5.1: KHMDS / tetrahydrofuran / 1.5 h / 20 °C

5.2: 41 percent / tetrahydrofuran / 1 h / 20 °C

With lithium aluminium tetrahydride; tin(II) trifluoromethanesulfonate; potassium hexamethylsilazane; triethylamine; palladium diacetate; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo050503t

Reference yield:

: 859163-70-5
N-[2-(5-chloro-1H-indol-3-yl)ethyl]-4-nitrobenzenesulfonylamide

: 859163-73-8
1-[6-chloro-2-(4-nitrobenzenesulfonyl)-1-vinyl-1,2,3,4-tetrahydro-β-carbolin-9-yl]-propenone

Guidance literature:: Multi-step reaction with 3 steps

1.1: 83 percent / Et₃N / Pd(OAc)2 / acetonitrile / 2 h / 20 °C

2.1: 94 percent / Sn(OTf)2 / CH₂Cl₂ / 2 h / 0 °C

3.1: KHMDS / tetrahydrofuran / 1.5 h / 20 °C

3.2: 41 percent / tetrahydrofuran / 1 h / 20 °C

With tin(II) trifluoromethanesulfonate; potassium hexamethylsilazane; triethylamine; palladium diacetate; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo050503t