5-chloro-3-ethyl-N-(2-(4-(pyrrolidin-1-yl)phenyl)ethyl)-1H-indole-2-carboxamide

Base Information

Chemical Name:5-chloro-3-ethyl-N-(2-(4-(pyrrolidin-1-yl)phenyl)ethyl)-1H-indole-2-carboxamide
CAS No.:1377838-03-3
Molecular Formula:C₂₃H₂₆ClN₃O
Molecular Weight:395.932
Hs Code.:

Synonyms:5-chloro-3-ethyl-N-(2-(4-(pyrrolidin-1-yl)phenyl)ethyl)-1H-indole-2-carboxamide

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Chemical Property of 5-chloro-3-ethyl-N-(2-(4-(pyrrolidin-1-yl)phenyl)ethyl)-1H-indole-2-carboxamide

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Technology Process of 5-chloro-3-ethyl-N-(2-(4-(pyrrolidin-1-yl)phenyl)ethyl)-1H-indole-2-carboxamide

There total 6 articles about 5-chloro-3-ethyl-N-(2-(4-(pyrrolidin-1-yl)phenyl)ethyl)-1H-indole-2-carboxamide 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: 66.0%

: 663926-22-5
2-(4-(pyrrolidin-1-yl)phenyl)ethanamine

: 446830-67-7
5-chloro-3-ethyl-1H-indole-2-carboxylic acid

: 1377838-03-3
5-chloro-3-ethyl-N-(2-(4-(pyrrolidin-1-yl)phenyl)ethyl)-1H-indole-2-carboxamide

Guidance literature:: With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.1021/jm201485c

Reference yield:

: 41841-16-1
(4-bromo-phenyl)-acetic acid methyl ester

: 1377838-03-3
5-chloro-3-ethyl-N-(2-(4-(pyrrolidin-1-yl)phenyl)ethyl)-1H-indole-2-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 °C

2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 3 h / 0 - 20 °C

3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; XPhos / toluene / 110 °C

4: hydrazine hydrate / ethanol / Reflux

5: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium aluminium tetrahydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; caesium carbonate; hydrazine hydrate; triethylamine; triphenylphosphine; diethylazodicarboxylate; XPhos; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; toluene; 2: Mitsunobu reaction / 3: Buchwald-Hartwig amination;
DOI:10.1021/jm201485c

Reference yield:

: 4654-39-1
4-bromophenethanol

: 1377838-03-3
5-chloro-3-ethyl-N-(2-(4-(pyrrolidin-1-yl)phenyl)ethyl)-1H-indole-2-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 3 h / 0 - 20 °C

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; XPhos / toluene / 110 °C

3: hydrazine hydrate / ethanol / Reflux

4: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; caesium carbonate; hydrazine hydrate; triethylamine; triphenylphosphine; diethylazodicarboxylate; XPhos; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; toluene; 1: Mitsunobu reaction / 2: Buchwald-Hartwig amination;
DOI:10.1021/jm201485c