N-(2-(4-bromo-1H-indol-3-yl)ethyl)-N-(4-methoxybenzyl)-3-(3,4,5-trimethoxyphenyl)propiolamide

Base Information

• Chemical Name: N-(2-(4-bromo-1H-indol-3-yl)ethyl)-N-(4-methoxybenzyl)-3-(3,4,5-trimethoxyphenyl)propiolamide
• CAS No.: 1294437-51-6
• Molecular Formula: C₃₀H₂₉BrN₂O₅
• Molecular Weight: 577.475

Synonyms:N-(2-(4-bromo-1H-indol-3-yl)ethyl)-N-(4-methoxybenzyl)-3-(3,4,5-trimethoxyphenyl)propiolamide

Chemical Property of N-(2-(4-bromo-1H-indol-3-yl)ethyl)-N-(4-methoxybenzyl)-3-(3,4,5-trimethoxyphenyl)propiolamide

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Technology Process of N-(2-(4-bromo-1H-indol-3-yl)ethyl)-N-(4-methoxybenzyl)-3-(3,4,5-trimethoxyphenyl)propiolamide

There total 4 articles about N-(2-(4-bromo-1H-indol-3-yl)ethyl)-N-(4-methoxybenzyl)-3-(3,4,5-trimethoxyphenyl)propiolamide 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: 57.0%

3-(3,4,5-trimethoxyphenyl)propiolic acid (4698-21-9) + 2-(4-bromo-1H-indol-3-yl)-N-(4-methoxybenzyl)ethanamine (1294437-40-3) → N-(2-(4-bromo-1H-indol-3-yl)ethyl)-N-(4-methoxybenzyl)-3-(3,4,5-trimethoxyphenyl)propiolamide (1294437-51-6)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 25 ℃;

DOI:10.1002/ejoc.201001669

Reference yield:

2-(4-bromo-1H-indol-3-yl)-N-(4-methoxybenzylidene)ethanamine → N-(2-(4-bromo-1H-indol-3-yl)ethyl)-N-(4-methoxybenzyl)-3-(3,4,5-trimethoxyphenyl)propiolamide (1294437-51-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / ethanol / 25 °C

2: dmap; dicyclohexyl-carbodiimide / dichloromethane / 25 °C

With dmap; sodium tetrahydroborate; dicyclohexyl-carbodiimide; In ethanol; dichloromethane;

DOI:10.1002/ejoc.201001669

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → N-(2-(4-bromo-1H-indol-3-yl)ethyl)-N-(4-methoxybenzyl)-3-(3,4,5-trimethoxyphenyl)propiolamide (1294437-51-6)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene / 3 h / Reflux

2: sodium tetrahydroborate / ethanol / 25 °C

3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 25 °C

With dmap; sodium tetrahydroborate; dicyclohexyl-carbodiimide; In ethanol; dichloromethane; toluene;

DOI:10.1002/ejoc.201001669

upstream raw materials:

3-(3,4,5-trimethoxyphenyl)propiolic acid

2-(4-bromo-1H-indol-3-yl)-N-(4-methoxybenzyl)ethanamine

4-methoxy-benzaldehyde

2-(4-bromo-1H-indol-3-yl)ethan-1-amine

Downstream raw materials:

(Z)-5-(4-methoxybenzyl)-7-(3,4,5-trimethoxybenzylidene)-3,4,5,7-tetrahydroazocino[4,5,6-cd]indol-6(1H)-one

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