3-[(3-formyl-6-methoxy-2-quinolinyl)ethynyl]-N-[2-(4-morpholinyl)ethyl]benzamide

Base Information

Chemical Name:3-[(3-formyl-6-methoxy-2-quinolinyl)ethynyl]-N-[2-(4-morpholinyl)ethyl]benzamide
CAS No.:1437302-32-3
Molecular Formula:C₂₆H₂₅N₃O₄
Molecular Weight:443.502
Hs Code.:

Synonyms:3-[(3-formyl-6-methoxy-2-quinolinyl)ethynyl]-N-[2-(4-morpholinyl)ethyl]benzamide

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Chemical Property of 3-[(3-formyl-6-methoxy-2-quinolinyl)ethynyl]-N-[2-(4-morpholinyl)ethyl]benzamide

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Technology Process of 3-[(3-formyl-6-methoxy-2-quinolinyl)ethynyl]-N-[2-(4-morpholinyl)ethyl]benzamide

There total 6 articles about 3-[(3-formyl-6-methoxy-2-quinolinyl)ethynyl]-N-[2-(4-morpholinyl)ethyl]benzamide 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: 70.0%

: 73568-29-3
2-chloro-6-methoxyquinolin-3-carboxaldehyde

: 1437302-54-9
3-ethynyl-N-[2-(4-morpholinyl)ethyl]benzamide

: 1437302-32-3
3-[(3-formyl-6-methoxy-2-quinolinyl)ethynyl]-N-[2-(4-morpholinyl)ethyl]benzamide

Guidance literature:: With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1021/ja403074j

Reference yield:

: 77123-59-2
methyl 3-<(trimethylsilyl)ethynyl>benzoate

: 1437302-32-3
3-[(3-formyl-6-methoxy-2-quinolinyl)ethynyl]-N-[2-(4-morpholinyl)ethyl]benzamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

2.1: trimethylaluminum / toluene / 0.25 h / Inert atmosphere

2.2: 7 h / 20 - 120 °C / Inert atmosphere

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; trimethylaluminum; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 3.1: |Sonogashira Cross-Coupling;
DOI:10.1021/ja403074j

Reference yield:

: 618-89-3
methyl 3-bromobenzoate

: 1437302-32-3
3-[(3-formyl-6-methoxy-2-quinolinyl)ethynyl]-N-[2-(4-morpholinyl)ethyl]benzamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide; triethylamine / acetonitrile / 4 h / Reflux; Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

3.1: trimethylaluminum / toluene / 0.25 h / Inert atmosphere

3.2: 7 h / 20 - 120 °C / Inert atmosphere

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; trimethylaluminum; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: |Sonogashira Cross-Coupling / 4.1: |Sonogashira Cross-Coupling;
DOI:10.1021/ja403074j