Benzonitrile, 4-(3-phenyl-1H-indol-2-yl)-

Base Information

• Chemical Name: Benzonitrile, 4-(3-phenyl-1H-indol-2-yl)-
• CAS No.: 144054-19-3
• Molecular Formula: C21H14N2
• Molecular Weight: 294.356
• Mol file: 144054-19-3.mol

Synonyms:

Chemical Property of Benzonitrile, 4-(3-phenyl-1H-indol-2-yl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzonitrile, 4-(3-phenyl-1H-indol-2-yl)-

There total 3 articles about Benzonitrile, 4-(3-phenyl-1H-indol-2-yl)- 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: 46.0%

4-(2-phenylethynyl)benzonitrile (29822-79-5) + 2-iodophenylamine (615-43-0) → 4-(3-phenyl-1H-indol-2-yl)benzonitrile (144054-19-3) + 4-(2-phenyl-1H-indol-3-yl)benzonitrile

Guidance literature:

With palladium diacetate; sodium carbonate; triphenylphosphine; lithium chloride; In N,N-dimethyl-formamide; at 100 ℃; for 24h; regioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.joc.1c02560

Reference yield:

4-iodobenzonitrile (3058-39-7) → 4-(3-phenyl-1H-indol-2-yl)benzonitrile (144054-19-3) + 4-(2-phenyl-1H-indol-3-yl)benzonitrile

Guidance literature:

Multi-step reaction with 2 steps

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

2: palladium diacetate; triphenylphosphine; sodium carbonate; tetrabutyl-ammonium chloride / N,N-dimethyl-formamide / 24 h / 80 °C / Inert atmosphere

With copper(l) iodide; tetrabutyl-ammonium chloride; palladium diacetate; sodium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; 1: |Sonogashira Cross-Coupling / 2: |Larock Annulation;

DOI:10.1021/jo402304s

Reference yield:

phenylacetylene (536-74-3) → 4-(3-phenyl-1H-indol-2-yl)benzonitrile (144054-19-3) + 4-(2-phenyl-1H-indol-3-yl)benzonitrile

Guidance literature:

Multi-step reaction with 2 steps

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

2: palladium diacetate; triphenylphosphine; sodium carbonate; tetrabutyl-ammonium chloride / N,N-dimethyl-formamide / 24 h / 80 °C / Inert atmosphere

With copper(l) iodide; tetrabutyl-ammonium chloride; palladium diacetate; sodium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; 1: |Sonogashira Cross-Coupling / 2: |Larock Annulation;

DOI:10.1021/jo402304s

upstream raw materials:

4-iodobenzonitrile

phenylacetylene

4-(2-phenylethynyl)benzonitrile

2-iodophenylamine

Refernces

• 1、 Chuawong, Pitak,Gable, Kevin P.,Yiamsawat, Kanyapat. "Dissecting the Electronic Contribution to the Regioselectivity of the Larock Heteroannulation Reaction in the Oxidative Addition and Carbopalladation Steps". . p. 1218 - 1229. Retrieved 2022/01/27.