ethyl 1-allyloxycarbonyl-3-[2-(4-methoxybenzyloxy)phenyl]-2-oxoindole-3-carboxylate

Base Information

Chemical Name:ethyl 1-allyloxycarbonyl-3-[2-(4-methoxybenzyloxy)phenyl]-2-oxoindole-3-carboxylate
CAS No.:935846-45-0
Molecular Formula:C₂₉H₂₇NO₇
Molecular Weight:501.536
Hs Code.:

Synonyms:ethyl 1-allyloxycarbonyl-3-[2-(4-methoxybenzyloxy)phenyl]-2-oxoindole-3-carboxylate

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Chemical Property of ethyl 1-allyloxycarbonyl-3-[2-(4-methoxybenzyloxy)phenyl]-2-oxoindole-3-carboxylate

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Technology Process of ethyl 1-allyloxycarbonyl-3-[2-(4-methoxybenzyloxy)phenyl]-2-oxoindole-3-carboxylate

There total 8 articles about ethyl 1-allyloxycarbonyl-3-[2-(4-methoxybenzyloxy)phenyl]-2-oxoindole-3-carboxylate 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: 90.0%

: 935846-42-7
ethyl 3-[2-(4-methoxybenzyloxy)phenyl]-2-oxoindole-3-carboxylate

: 2937-50-0
Allyl chloroformate

: 935846-45-0
ethyl 1-allyloxycarbonyl-3-[2-(4-methoxybenzyloxy)phenyl]-2-oxoindole-3-carboxylate

Guidance literature:: ethyl 3-[2-(4-methoxybenzyloxy)phenyl]-2-oxoindole-3-carboxylate; Allyl chloroformate; With sodium hydride; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃;

With dmap; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; Further stages.;
DOI:10.1021/jo062627r

Reference yield:

: 935846-39-2
2-(2-((4-methoxybenzyl)oxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 935846-45-0
ethyl 1-allyloxycarbonyl-3-[2-(4-methoxybenzyloxy)phenyl]-2-oxoindole-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 81 percent / aq. potassium carbonate / PdCl₂(dppf)*CH₂Cl₂ / 1,2-dimethoxy-ethane / 85 °C

2.1: tert-butyl hypochlorite / CH₂Cl₂ / 4 h / 20 °C

2.2: 87 percent / HCl / ethanol; CH₂Cl₂; diethyl ether

3.1: sodium hydride / tetrahydrofuran; CH₂Cl₂; various solvent(s) / 0 - 20 °C

3.2: 90 percent / 4-(dimethylamino)pyridine / tetrahydrofuran; CH₂Cl₂; various solvent(s) / 0 - 20 °C

With tert-butylhypochlorite; sodium hydride; potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/jo062627r

Reference yield:

: 3770-50-1,117770-52-2
2-carbethoxyindole

: 935846-45-0
ethyl 1-allyloxycarbonyl-3-[2-(4-methoxybenzyloxy)phenyl]-2-oxoindole-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-iodosuccinimide / dimethylformamide / 0 - 20 °C

1.2: 93 percent / sodium thiosulfate / dimethylformamide; H₂O / 1 h

2.1: 81 percent / aq. potassium carbonate / PdCl₂(dppf)*CH₂Cl₂ / 1,2-dimethoxy-ethane / 85 °C

3.1: tert-butyl hypochlorite / CH₂Cl₂ / 4 h / 20 °C

3.2: 87 percent / HCl / ethanol; CH₂Cl₂; diethyl ether

4.1: sodium hydride / tetrahydrofuran; CH₂Cl₂; various solvent(s) / 0 - 20 °C

4.2: 90 percent / 4-(dimethylamino)pyridine / tetrahydrofuran; CH₂Cl₂; various solvent(s) / 0 - 20 °C

With N-iodo-succinimide; tert-butylhypochlorite; sodium hydride; potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo062627r