{4-[3-(4-azidomethylphenylethynyl)-5-isopropyl-4-methoxymethoxybenzyl]-3,5-dimethylphenoxy}acetic acid methyl ester

Base Information

Chemical Name:{4-[3-(4-azidomethylphenylethynyl)-5-isopropyl-4-methoxymethoxybenzyl]-3,5-dimethylphenoxy}acetic acid methyl ester
CAS No.:851227-54-8
Molecular Formula:C₃₂H₃₅N₃O₅
Molecular Weight:541.647
Hs Code.:

Synonyms:{4-[3-(4-azidomethylphenylethynyl)-5-isopropyl-4-methoxymethoxybenzyl]-3,5-dimethylphenoxy}acetic acid methyl ester

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Chemical Property of {4-[3-(4-azidomethylphenylethynyl)-5-isopropyl-4-methoxymethoxybenzyl]-3,5-dimethylphenoxy}acetic acid methyl ester

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Technology Process of {4-[3-(4-azidomethylphenylethynyl)-5-isopropyl-4-methoxymethoxybenzyl]-3,5-dimethylphenoxy}acetic acid methyl ester

There total 9 articles about {4-[3-(4-azidomethylphenylethynyl)-5-isopropyl-4-methoxymethoxybenzyl]-3,5-dimethylphenoxy}acetic 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:

: 863640-77-1
((4-iodobenzyl)oxy)triisopropylsilane

: 851227-54-8
{4-[3-(4-azidomethylphenylethynyl)-5-isopropyl-4-methoxymethoxybenzyl]-3,5-dimethylphenoxy}acetic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1.18 g / PdCl₂(PPh₃)2; CuI; diethylamine / 5 h / 20 °C

2.1: 97 percent / aq. KOH / methanol / 2 h / 20 °C

3.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

3.2: methoxy-9-BBN / tetrahydrofuran; toluene; hexane / 2 h / -78 °C

3.3: 69 percent / PdCl₂(PPh₃)2 / tetrahydrofuran; toluene; hexane / 18 h / Heating

4.1: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C

5.1: chlorotrimethylsilane / dimethylsulfoxide / 0.5 h / 20 °C

6.1: 183 mg / NaN₃ / dimethylsulfoxide / 0.58 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide; copper(l) iodide; chloro-trimethyl-silane; sodium azide; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; diethylamine; In tetrahydrofuran; methanol; dimethyl sulfoxide; toluene; 1.1: Sonogashira coupling / 3.3: Suzuki-Miyaura coupling;
DOI:10.1021/ja0440093

Reference yield:

: 851227-22-0
(4-ethynylbenzyloxy)triisopropylsilane

: 851227-54-8
{4-[3-(4-azidomethylphenylethynyl)-5-isopropyl-4-methoxymethoxybenzyl]-3,5-dimethylphenoxy}acetic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

1.2: methoxy-9-BBN / tetrahydrofuran; toluene; hexane / 2 h / -78 °C

1.3: 69 percent / PdCl₂(PPh₃)2 / tetrahydrofuran; toluene; hexane / 18 h / Heating

2.1: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C

3.1: chlorotrimethylsilane / dimethylsulfoxide / 0.5 h / 20 °C

4.1: 183 mg / NaN₃ / dimethylsulfoxide / 0.58 h / 20 °C

With chloro-trimethyl-silane; sodium azide; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; In tetrahydrofuran; dimethyl sulfoxide; toluene; 1.3: Suzuki-Miyaura coupling;
DOI:10.1021/ja0440093

Reference yield:

: 863640-78-2
1-triisopropylsilanyloxymethyl-4-trimethylsilanylethynyl-benzene

: 851227-54-8
{4-[3-(4-azidomethylphenylethynyl)-5-isopropyl-4-methoxymethoxybenzyl]-3,5-dimethylphenoxy}acetic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 97 percent / aq. KOH / methanol / 2 h / 20 °C

2.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

2.2: methoxy-9-BBN / tetrahydrofuran; toluene; hexane / 2 h / -78 °C

2.3: 69 percent / PdCl₂(PPh₃)2 / tetrahydrofuran; toluene; hexane / 18 h / Heating

3.1: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C

4.1: chlorotrimethylsilane / dimethylsulfoxide / 0.5 h / 20 °C

5.1: 183 mg / NaN₃ / dimethylsulfoxide / 0.58 h / 20 °C

With potassium hydroxide; chloro-trimethyl-silane; sodium azide; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; In tetrahydrofuran; methanol; dimethyl sulfoxide; toluene; 2.3: Suzuki-Miyaura coupling;
DOI:10.1021/ja0440093