3-(phenylethynyl)-1-(2-(trimethylsilyl)ethoxymethyl)-1H-pyrrol-2-carbaldehyde

Base Information

Chemical Name:3-(phenylethynyl)-1-(2-(trimethylsilyl)ethoxymethyl)-1H-pyrrol-2-carbaldehyde
CAS No.:1191423-03-6
Molecular Formula:C₁₉H₂₃NO₂Si
Molecular Weight:325.483
Hs Code.:

Synonyms:3-(phenylethynyl)-1-(2-(trimethylsilyl)ethoxymethyl)-1H-pyrrol-2-carbaldehyde

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Chemical Property of 3-(phenylethynyl)-1-(2-(trimethylsilyl)ethoxymethyl)-1H-pyrrol-2-carbaldehyde

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Technology Process of 3-(phenylethynyl)-1-(2-(trimethylsilyl)ethoxymethyl)-1H-pyrrol-2-carbaldehyde

There total 2 articles about 3-(phenylethynyl)-1-(2-(trimethylsilyl)ethoxymethyl)-1H-pyrrol-2-carbaldehyde 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: 96.0%

: 1191422-74-8
3-bromo-1-(2-(trimethylsilyl)ethoxymethyl)-1H-pyrrol-2-carbaldehyde

: 536-74-3
phenylacetylene

: 1191423-03-6
3-(phenylethynyl)-1-(2-(trimethylsilyl)ethoxymethyl)-1H-pyrrol-2-carbaldehyde

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 100 ℃; for 5h; Inert atmosphere;
DOI:10.1248/cpb.59.579

Reference yield:

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 408359-07-9
3-bromo-1H-pyrrole-2-carbaldehyde

: 1191423-03-6
3-(phenylethynyl)-1-(2-(trimethylsilyl)ethoxymethyl)-1H-pyrrol-2-carbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium tert-butylate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

1.2: 1 h / 0 °C / Inert atmosphere

2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 5 h / 100 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium tert-butylate; triethylamine; In N,N-dimethyl-formamide; 2.1: Sonogashira coupling;
DOI:10.1248/cpb.59.579

Reference yield:

: 1191423-03-6
3-(phenylethynyl)-1-(2-(trimethylsilyl)ethoxymethyl)-1H-pyrrol-2-carbaldehyde

: ethyl [4-(3-phenethyl-1-(2-(trimethylsilyl)ethoxymethyl)-1H-pyrrol-2-yl)-1H-imidazo[4,5-c]pyridin-2-yl]carbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: Inert atmosphere; Reflux

2.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 760.05 Torr

With palladium 10% on activated carbon; hydrogen; dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In ethanol; 1.1: Pictet-Spengler cyclisation;
DOI:10.1248/cpb.59.579