5-methoxy-1-ethyl-3-phenylethynyl-1H-indole-2-carboxylic acid methyl ester

Base Information

Chemical Name:5-methoxy-1-ethyl-3-phenylethynyl-1H-indole-2-carboxylic acid methyl ester
CAS No.:1316759-15-5
Molecular Formula:C₂₁H₁₉NO₃
Molecular Weight:333.387
Hs Code.:

Synonyms:5-methoxy-1-ethyl-3-phenylethynyl-1H-indole-2-carboxylic acid methyl ester

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Chemical Property of 5-methoxy-1-ethyl-3-phenylethynyl-1H-indole-2-carboxylic acid methyl ester

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Technology Process of 5-methoxy-1-ethyl-3-phenylethynyl-1H-indole-2-carboxylic acid methyl ester

There total 4 articles about 5-methoxy-1-ethyl-3-phenylethynyl-1H-indole-2-carboxylic acid methyl ester 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: 84.0%

: 1316759-03-1
3-iodo-5-methoxy-1-ethyl-1H-indole-2-carboxylic acid methyl ester

: 536-74-3
phenylacetylene

: 1316759-15-5
5-methoxy-1-ethyl-3-phenylethynyl-1H-indole-2-carboxylic acid methyl ester

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 20 ℃; for 6h; Inert atmosphere;
DOI:10.1007/s12039-016-1070-8

Reference yield:

: 1316758-95-8
C₁₁H₁₀INO₃

: 1316759-15-5
5-methoxy-1-ethyl-3-phenylethynyl-1H-indole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere

1.2: 3 h / 0 - 20 °C / Inert atmosphere

2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 0.25 h / Inert atmosphere

2.2: 6 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sodium hydride; triethylamine; In N,N-dimethyl-formamide; 2.2: Sonogashira coupling;
DOI:10.1016/j.bmcl.2011.05.088

Reference yield:

: 4382-54-1
5-methoxy-1H-indole-2-carboxylic acid

: 1316759-15-5
5-methoxy-1-ethyl-3-phenylethynyl-1H-indole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: sulfuric acid / 24 h / Reflux

2.1: potassium hydroxide / N,N-dimethyl-formamide / 0.25 h

2.2: 3 h

3.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere

3.2: 3 h / 0 - 20 °C / Inert atmosphere

4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 0.25 h / Inert atmosphere

4.2: 6 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sulfuric acid; sodium hydride; triethylamine; potassium hydroxide; In N,N-dimethyl-formamide; 4.2: Sonogashira coupling;
DOI:10.1016/j.bmcl.2011.05.088