ethyl 1-cyclopropyl-6-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Base Information

Chemical Name:ethyl 1-cyclopropyl-6-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate
CAS No.:1616491-57-6
Molecular Formula:C₂₂H₂₀FNO₃
Molecular Weight:365.404
Hs Code.:

Synonyms:ethyl 1-cyclopropyl-6-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

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Chemical Property of ethyl 1-cyclopropyl-6-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Chemical Property:

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Technology Process of ethyl 1-cyclopropyl-6-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

There total 6 articles about ethyl 1-cyclopropyl-6-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate 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: 43.0%

: 223761-28-2
(4-fluorobenzyl)zinc(II) bromide

: 6-iodo-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

: 1616491-57-6
ethyl 1-cyclopropyl-6-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

: 1616491-27-0
4-fluorobenzyl-1-cyclopropyl-6-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Guidance literature:: With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; In tetrahydrofuran; at 65 ℃; for 3h; Inert atmosphere;
DOI:10.1016/j.bmc.2014.05.028

Reference yield:

: 124700-41-0
2-fluoro-5-iodobenzoic acid

: 1616491-57-6
ethyl 1-cyclopropyl-6-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

: 1616491-27-0
4-fluorobenzyl-1-cyclopropyl-6-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: thionyl chloride / Reflux

2: triethylamine / toluene / Reflux

3: ethanol; diethyl ether / 20 °C

4: potassium carbonate / N,N-dimethyl-formamide / 0.67 h / 100 °C

5: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane / tetrahydrofuran / 3 h / 65 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; thionyl chloride; trifuran-2-yl-phosphane; potassium carbonate; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide; toluene; 5: |Negishi Coupling;
DOI:10.1016/j.bmc.2014.05.028

Reference yield:

: 186584-73-6
2-fluoro-5-iodobenzoyl chloride

: 1616491-57-6
ethyl 1-cyclopropyl-6-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

: 1616491-27-0
4-fluorobenzyl-1-cyclopropyl-6-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine / toluene / Reflux

2: ethanol; diethyl ether / 20 °C

3: potassium carbonate / N,N-dimethyl-formamide / 0.67 h / 100 °C

4: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane / tetrahydrofuran / 3 h / 65 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; potassium carbonate; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide; toluene; 4: |Negishi Coupling;
DOI:10.1016/j.bmc.2014.05.028