N-[(5,8-dimethoxy-7-nitroquinolin-2-yl)ethynyl]-N-[2-(prop-1-ynyl)phenyl]-p-toluenesulfonamide

Base Information

Chemical Name:N-[(5,8-dimethoxy-7-nitroquinolin-2-yl)ethynyl]-N-[2-(prop-1-ynyl)phenyl]-p-toluenesulfonamide
CAS No.:1311160-02-7
Molecular Formula:C₂₉H₂₃N₃O₆S
Molecular Weight:541.584
Hs Code.:

Synonyms:N-[(5,8-dimethoxy-7-nitroquinolin-2-yl)ethynyl]-N-[2-(prop-1-ynyl)phenyl]-p-toluenesulfonamide

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Chemical Property of N-[(5,8-dimethoxy-7-nitroquinolin-2-yl)ethynyl]-N-[2-(prop-1-ynyl)phenyl]-p-toluenesulfonamide

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Technology Process of N-[(5,8-dimethoxy-7-nitroquinolin-2-yl)ethynyl]-N-[2-(prop-1-ynyl)phenyl]-p-toluenesulfonamide

There total 13 articles about N-[(5,8-dimethoxy-7-nitroquinolin-2-yl)ethynyl]-N-[2-(prop-1-ynyl)phenyl]-p-toluenesulfonamide 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: 90.0%

: 1311160-11-8
2-iodo-5,8-dimethoxy-7-nitroquinoline

: 497236-39-2
N-ethynyl-N-[2-(prop-1-yn-1-yl)phenyl]-p-toluenesulfonamide

: 1311160-02-7
N-[(5,8-dimethoxy-7-nitroquinolin-2-yl)ethynyl]-N-[2-(prop-1-ynyl)phenyl]-p-toluenesulfonamide

Guidance literature:: N-ethynyl-N-[2-(prop-1-yn-1-yl)phenyl]-p-toluenesulfonamide; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - -40 ℃; for 0.55h;

With zinc dibromide; In tetrahydrofuran; for 0.5h;

2-iodo-5,8-dimethoxy-7-nitroquinoline; With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine; In tetrahydrofuran; for 3h;
DOI:10.1002/ejoc.201100131

Reference yield:

: 1311160-08-3
5,8-dimethoxy-7-nitroquinolin-2(1H)-one

: 1311160-02-7
N-[(5,8-dimethoxy-7-nitroquinolin-2-yl)ethynyl]-N-[2-(prop-1-ynyl)phenyl]-p-toluenesulfonamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: trichlorophosphate / N,N-dimethyl-formamide / 0.5 h / 120 °C

2.1: acetyl chloride; sodium iodide / acetonitrile / 3.5 h / 60 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.55 h / -78 - -40 °C

3.2: 0.5 h

3.3: 3 h

With acetyl chloride; sodium iodide; lithium hexamethyldisilazane; trichlorophosphate; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; 3.3: Negishi coupling reaction;
DOI:10.1002/ejoc.201100131

Reference yield:

: 15174-07-9
1,4-dimethoxy-2,6-dinitrobenzene

: 1311160-02-7
N-[(5,8-dimethoxy-7-nitroquinolin-2-yl)ethynyl]-N-[2-(prop-1-ynyl)phenyl]-p-toluenesulfonamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: palladium 10% on activated carbon; cyclohexene / ethanol / 5 h / 45 °C

2.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 14.5 h / 0 - 20 °C

3.1: sulfuric acid / 2 h / 20 °C

4.1: trichlorophosphate / N,N-dimethyl-formamide / 0.5 h / 120 °C

5.1: acetyl chloride; sodium iodide / acetonitrile / 3.5 h / 60 °C

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.55 h / -78 - -40 °C

6.2: 0.5 h

6.3: 3 h

With dmap; sulfuric acid; palladium 10% on activated carbon; acetyl chloride; dicyclohexyl-carbodiimide; sodium iodide; lithium hexamethyldisilazane; cyclohexene; trichlorophosphate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3.1: Knorr Quinoline synthesis / 6.3: Negishi coupling reaction;
DOI:10.1002/ejoc.201100131