3-(1H-indol-3-yl)-4-(1-(3-phenylethyl)-1H-1,2,3-triazol-4-yl)-N-methylmaleimide

Base Information

• Chemical Name: 3-(1H-indol-3-yl)-4-(1-(3-phenylethyl)-1H-1,2,3-triazol-4-yl)-N-methylmaleimide
• CAS No.: 1359754-67-8
• Molecular Formula: C₂₃H₁₉N₅O₂
• Molecular Weight: 397.436
• Mol file: 1359754-67-8.mol

Synonyms:

Chemical Property of 3-(1H-indol-3-yl)-4-(1-(3-phenylethyl)-1H-1,2,3-triazol-4-yl)-N-methylmaleimide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(1H-indol-3-yl)-4-(1-(3-phenylethyl)-1H-1,2,3-triazol-4-yl)-N-methylmaleimide

There total 4 articles about 3-(1H-indol-3-yl)-4-(1-(3-phenylethyl)-1H-1,2,3-triazol-4-yl)-N-methylmaleimide 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:

phenethyl azide (6926-44-9) + C15H10N2O2 → 3-(1H-indol-3-yl)-4-(1-(3-phenylethyl)-1H-1,2,3-triazol-4-yl)-N-methylmaleimide (1359754-67-8)

Guidance literature:

With copper(ll) sulfate pentahydrate; ascorbic acid sodium salt; In tetrahydrofuran; methanol; at 20 ℃;

DOI:10.1039/c1cc15851a

Reference yield:

4-chloro-3-(1H-indol-3-yl)-1-methyl-1H-pyrrole-2,5-dione (174574-69-7) → 3-(1H-indol-3-yl)-4-(1-(3-phenylethyl)-1H-1,2,3-triazol-4-yl)-N-methylmaleimide (1359754-67-8)

Guidance literature:

Multi-step reaction with 3 steps

1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran; methanol

3: copper(ll) sulfate pentahydrate; ascorbic acid sodium salt / tetrahydrofuran; methanol / 20 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(ll) sulfate pentahydrate; ascorbic acid sodium salt; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; methanol; 1: Sonogashira coupling;

DOI:10.1039/c1cc15851a

Reference yield:

3,4-dichloro-1-methyl-pyrrole-2,5-dione (1123-61-1) → 3-(1H-indol-3-yl)-4-(1-(3-phenylethyl)-1H-1,2,3-triazol-4-yl)-N-methylmaleimide (1359754-67-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ethylmagnesium bromide / tetrahydrofuran / 1 h / 60 °C

1.2: 1 h / 65 °C

2.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran; methanol

4.1: copper(ll) sulfate pentahydrate; ascorbic acid sodium salt / tetrahydrofuran; methanol / 20 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(ll) sulfate pentahydrate; ascorbic acid sodium salt; ethylmagnesium bromide; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; methanol; 2.1: Sonogashira coupling;

DOI:10.1039/c1cc15851a

upstream raw materials:

3,4-dichloro-1-methyl-pyrrole-2,5-dione

phenethyl azide

3-(1H-indol-3-yl)-1-methyl-4-((trimethylsilyl)ethynyl)-1H-pyrrole-2,5-dione

4-chloro-3-(1H-indol-3-yl)-1-methyl-1H-pyrrole-2,5-dione

Downstream raw materials:

3-(1H-indol-3-yl)-4-(1-(2-phenylethyl)-1H-1,2,3-triazol-4-yl)-maleimide