2-Phenyl-3-(pyridin-2-yl)-1h-indole

Base Information

• Chemical Name: 2-Phenyl-3-(pyridin-2-yl)-1h-indole
• CAS No.: 91025-04-6
• Molecular Formula: C19H14N2
• Molecular Weight: 270.334
• European Community (EC) Number: 620-463-8
• NSC Number: 146505
• DSSTox Substance ID: DTXSID70301814
• Wikidata: Q82046105
• Mol file: 91025-04-6.mol

Synonyms:2-phenyl-3-(pyridin-2-yl)-1h-indole;91025-04-6;2-phenyl-3-pyridin-2-yl-1H-indole;NSC146505;starbld0045047;SCHEMBL9842999;2-phenyl-3-(2-pyridyl)indole;DTXSID70301814;AKOS002663448;2-phenyl-3-(2-pyridinyl)-1H-indole;NSC 146505;NSC-146505

Chemical Property of 2-Phenyl-3-(pyridin-2-yl)-1h-indole

Chemical Property:

• Vapor Pressure: 2.73E-08mmHg at 25°C
• Boiling Point: 462.4°Cat760mmHg
• Flash Point: 204.5°C
• Density: 1.197g/cm³
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 270.115698455
• Heavy Atom Count: 21
• Complexity: 337

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=C(C3=CC=CC=C3N2)C4=CC=CC=N4

Technology Process of 2-Phenyl-3-(pyridin-2-yl)-1h-indole

There total 6 articles about 2-Phenyl-3-(pyridin-2-yl)-1h-indole 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: 94.0%

2-bromo-pyridine (109-04-6) + o-(phenylethynyl)trifluoroacetanilide (143360-89-8) → 2-phenyl-3-(2-pyridyl)indole (91025-04-6)

Guidance literature:

With caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In acetonitrile; at 100 ℃; for 2h;

DOI:10.1055/s-2003-38079

Reference yield: 83.0%

2-chloropyridine (109-09-1) + o-(phenylethynyl)trifluoroacetanilide (143360-89-8) → 2-phenyl-3-(2-pyridyl)indole (91025-04-6)

Guidance literature:

With caesium carbonate; XPhos; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In acetonitrile; at 120 ℃; for 3h;

DOI:10.1002/adsc.200606060

Reference yield:

2-iodophenylamine (615-43-0) → 2-phenyl-3-(2-pyridyl)indole (91025-04-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: i-Pr₂NH; CuI / Pd(PPh₃)2Cl₂ / dimethylformamide

1.2: 87 percent / dimethylformamide / 1.5 h / 0 - 20 °C

2.1: tetrahydrofuran / 1.5 h / 0 °C

3.1: 87 percent / Cs₂CO₃ / Pd(PPh₃)4 / acetonitrile / 2 h / 100 °C

With copper(l) iodide; caesium carbonate; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; 1.2: Sonogashira coupling;

DOI:10.1055/s-2004-815993

upstream raw materials:

hydrogenchloride

1-phenyl-2-[2]pyridyl-ethanone-phenylhydrazone

water

2-bromo-pyridine

Downstream raw materials:

2-(2-aminobenzoyl)pyridine

benzoic acid-[2-(pyridine-2-carbonyl)-anilide]

Refernces

• 1、 Cacchi, Sandro,Fabrizi, Giancarlo,Parisi, Luca M.. "Preparation of indoles from o-alkynyltrifluoroacetanilides through the aminopalladation-reductive elimination process". . p. 1889 - 1894. Retrieved 2007/10/03.