trans-3-{2-[5-(4-methanesulfonylpiperazin-1-ylmethyl)-2-nitrophenyl]vinyl}-2-chloroquinoline

Base Information

Chemical Name:trans-3-{2-[5-(4-methanesulfonylpiperazin-1-ylmethyl)-2-nitrophenyl]vinyl}-2-chloroquinoline
CAS No.:850171-48-1
Molecular Formula:C₂₃H₂₃ClN₄O₄S
Molecular Weight:486.979
Hs Code.:

Synonyms:trans-3-{2-[5-(4-methanesulfonylpiperazin-1-ylmethyl)-2-nitrophenyl]vinyl}-2-chloroquinoline

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Chemical Property of trans-3-{2-[5-(4-methanesulfonylpiperazin-1-ylmethyl)-2-nitrophenyl]vinyl}-2-chloroquinoline

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Technology Process of trans-3-{2-[5-(4-methanesulfonylpiperazin-1-ylmethyl)-2-nitrophenyl]vinyl}-2-chloroquinoline

There total 6 articles about trans-3-{2-[5-(4-methanesulfonylpiperazin-1-ylmethyl)-2-nitrophenyl]vinyl}-2-chloroquinoline 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: 83.0%

: 850171-14-1
2-[5-(4-methanesulfonylpiperazin-1-ylmethyl)-2-nitrophenyl]-1-(2-chloroquinolin-3-yl)ethanol

: 850171-48-1
trans-3-{2-[5-(4-methanesulfonylpiperazin-1-ylmethyl)-2-nitrophenyl]vinyl}-2-chloroquinoline

Guidance literature:: 2-[5-(4-methanesulfonylpiperazin-1-ylmethyl)-2-nitrophenyl]-1-(2-chloroquinolin-3-yl)ethanol; With trifluoroacetic acid; In Isopropyl acetate; at 20 ℃; for 0.5h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In Isopropyl acetate; at 60 ℃; for 0.5h;
DOI:10.1021/jo0480545

Reference yield:

: 100-11-8
1-bromomethyl-4-nitro-benzene

: 850171-48-1
trans-3-{2-[5-(4-methanesulfonylpiperazin-1-ylmethyl)-2-nitrophenyl]vinyl}-2-chloroquinoline

Guidance literature:: Multi-step reaction with 5 steps

1.1: isopropyl acetate; aq. ethanol / 0.5 h / 20 °C

2.1: 900 mg / Et₃N / isopropyl acetate / 0.5 h

3.1: tetrahydrofuran / 0.5 h

3.2: 85 percent / I₂ / tetrahydrofuran / 3 h / 20 °C

4.1: 56 percent / tetrabutylammonium fluoride / isopropyl acetate / 0.5 h

5.1: CF₃CO₂H / isopropyl acetate / 0.5 h / 20 °C

5.2: 83 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / isopropyl acetate / 0.5 h / 60 °C

With tetrabutyl ammonium fluoride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; ethanol; Isopropyl acetate;
DOI:10.1021/jo0480545

Reference yield:

: 55276-43-2
4-methanesulfonylpiperazine

: 850171-48-1
trans-3-{2-[5-(4-methanesulfonylpiperazin-1-ylmethyl)-2-nitrophenyl]vinyl}-2-chloroquinoline

Guidance literature:: Multi-step reaction with 4 steps

1.1: 99 percent / Na₂CO₃ / dimethylformamide / 2 h / 20 °C

2.1: tetrahydrofuran / 0.5 h

2.2: 85 percent / I₂ / tetrahydrofuran / 3 h / 20 °C

3.1: 56 percent / tetrabutylammonium fluoride / isopropyl acetate / 0.5 h

4.1: CF₃CO₂H / isopropyl acetate / 0.5 h / 20 °C

4.2: 83 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / isopropyl acetate / 0.5 h / 60 °C

With tetrabutyl ammonium fluoride; sodium carbonate; trifluoroacetic acid; In tetrahydrofuran; Isopropyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo0480545