ethyl N-[1-(3-isopropyl-4-triisopropylsilanyloxybenzyl)-2-methyl-1H-indol-4-yl]malonamate

Base Information

Chemical Name:ethyl N-[1-(3-isopropyl-4-triisopropylsilanyloxybenzyl)-2-methyl-1H-indol-4-yl]malonamate
CAS No.:1000605-77-5
Molecular Formula:C₃₃H₄₈N₂O₄Si
Molecular Weight:564.841
Hs Code.:

Synonyms:ethyl N-[1-(3-isopropyl-4-triisopropylsilanyloxybenzyl)-2-methyl-1H-indol-4-yl]malonamate

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Chemical Property of ethyl N-[1-(3-isopropyl-4-triisopropylsilanyloxybenzyl)-2-methyl-1H-indol-4-yl]malonamate

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Technology Process of ethyl N-[1-(3-isopropyl-4-triisopropylsilanyloxybenzyl)-2-methyl-1H-indol-4-yl]malonamate

There total 8 articles about ethyl N-[1-(3-isopropyl-4-triisopropylsilanyloxybenzyl)-2-methyl-1H-indol-4-yl]malonamate 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: 71.0%

: 1000605-24-2
1-(3-isopropyl-4-triisopropylsilanyloxybenzyl)-2-methyl-1H-indol-4-ylamine

: 36239-09-5
ethyl chlorocarbonylacetate

: 1000605-77-5
ethyl N-[1-(3-isopropyl-4-triisopropylsilanyloxybenzyl)-2-methyl-1H-indol-4-yl]malonamate

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃; for 0.5h;
DOI:10.1016/j.bmc.2013.11.001

Reference yield:

: 26307-50-6
4-bromo-2-isopropyl-phenol

: 1000605-77-5
ethyl N-[1-(3-isopropyl-4-triisopropylsilanyloxybenzyl)-2-methyl-1H-indol-4-yl]malonamate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; pentane / 2 h / -78 °C

2.2: 4 h / -78 - 20 °C

3.1: thionyl chloride / dichloromethane / 2 h / 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 5 °C

4.2: 3 h / 5 °C

5.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; ethanol / 3 h / 20 °C

6.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C

With 1H-imidazole; n-butyllithium; thionyl chloride; palladium 10% on activated carbon; hydrogen; sodium hydride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; mineral oil; pentane;
DOI:10.1016/j.bmc.2013.11.001

Reference yield:

: 253329-09-8
4-bromo-2-isopropyl-1-triisopropylsilanyloxybenzene

: 1000605-77-5
ethyl N-[1-(3-isopropyl-4-triisopropylsilanyloxybenzyl)-2-methyl-1H-indol-4-yl]malonamate

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran; pentane / 2 h / -78 °C

1.2: 4 h / -78 - 20 °C

2.1: thionyl chloride / dichloromethane / 2 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 5 °C

3.2: 3 h / 5 °C

4.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; ethanol / 3 h / 20 °C

5.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C

With n-butyllithium; thionyl chloride; palladium 10% on activated carbon; hydrogen; sodium hydride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; mineral oil; pentane;
DOI:10.1016/j.bmc.2013.11.001