N-[2-(1-methoxy-1H-indol-2-yl)prop-2-en-1-yl]-N-{2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]phenyl}acetamide

Base Information

Chemical Name:N-[2-(1-methoxy-1H-indol-2-yl)prop-2-en-1-yl]-N-{2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]phenyl}acetamide
CAS No.:1310368-13-8
Molecular Formula:C₂₈H₃₀N₂O₄
Molecular Weight:458.557
Hs Code.:

Synonyms:N-[2-(1-methoxy-1H-indol-2-yl)prop-2-en-1-yl]-N-{2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]phenyl}acetamide

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Chemical Property of N-[2-(1-methoxy-1H-indol-2-yl)prop-2-en-1-yl]-N-{2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]phenyl}acetamide

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Technology Process of N-[2-(1-methoxy-1H-indol-2-yl)prop-2-en-1-yl]-N-{2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]phenyl}acetamide

There total 7 articles about N-[2-(1-methoxy-1H-indol-2-yl)prop-2-en-1-yl]-N-{2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]phenyl}acetamide 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: 60.0%

: 54698-11-2
1-methoxyindole

: 1310368-12-7
N-(2-bromoprop-2-en-1-yl)-N-{2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]phenyl}-acetamide

: 1310368-13-8
N-[2-(1-methoxy-1H-indol-2-yl)prop-2-en-1-yl]-N-{2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]phenyl}acetamide

: 1310368-11-6
(4Z)-4-[1-(1-methoxy-1H-indol-2-yl)-2-(tetrahydro-2H-pyran-2-yloxy)ethylidene]-3-methylidene-1-(prop-1-en-2-yl)-1,2,3,4-tetrahydroquinoline

Guidance literature:: 1-methoxyindole; With n-butyllithium; In tetrahydrofuran; hexane; at -20 ℃; for 0.5h; Inert atmosphere;

With triethyl borane; In tetrahydrofuran; hexane; at -20 - 20 ℃; for 1.5h; Inert atmosphere;

N-(2-bromoprop-2-en-1-yl)-N-{2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]phenyl}-acetamide; With dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; hexane; at 20 - 60 ℃; for 0.666667h; Inert atmosphere;
DOI:10.1002/ejoc.201200657

Reference yield:

: 1310368-12-7
N-(2-bromoprop-2-en-1-yl)-N-{2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]phenyl}-acetamide

: lithium triethyl(1-methoxyindol-2-yl)borate

: 1310368-13-8
N-[2-(1-methoxy-1H-indol-2-yl)prop-2-en-1-yl]-N-{2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]phenyl}acetamide

: 1310368-11-6
(4Z)-4-[1-(1-methoxy-1H-indol-2-yl)-2-(tetrahydro-2H-pyran-2-yloxy)ethylidene]-3-methylidene-1-(prop-1-en-2-yl)-1,2,3,4-tetrahydroquinoline

Guidance literature:: With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tris-(o-tolyl)phosphine; In tetrahydrofuran; hexane; at 20 - 60 ℃; for 0.666667h; Inert atmosphere;
DOI:10.1021/ol201107a

Reference yield:

: 287477-27-4
2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]aniline

: 1310368-13-8
N-[2-(1-methoxy-1H-indol-2-yl)prop-2-en-1-yl]-N-{2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]phenyl}acetamide

: 1310368-11-6
(4Z)-4-[1-(1-methoxy-1H-indol-2-yl)-2-(tetrahydro-2H-pyran-2-yloxy)ethylidene]-3-methylidene-1-(prop-1-en-2-yl)-1,2,3,4-tetrahydroquinoline

Guidance literature:: Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / 2 h / 20 °C / Cooling with ice

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / Cooling with ice

2.2: 2 h / 20 °C

3.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tris-(o-tolyl)phosphine / tetrahydrofuran; hexane / 0.67 h / 20 - 60 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydride; triethylamine; tris-(o-tolyl)phosphine; In tetrahydrofuran; hexane; dichloromethane; mineral oil;
DOI:10.1021/ol201107a