5-(Pyridin-3-yl)-1h-indole

Base Information

• Chemical Name: 5-(Pyridin-3-yl)-1h-indole
• CAS No.: 144104-49-4
• Molecular Formula: C₁₃H₁₀N₂
• Molecular Weight: 194.236
• Hs Code.: 2933990090
• ChEMBL ID: CHEMBL1435857
• DSSTox Substance ID: DTXSID90566327
• Wikidata: Q82451903
• Mol file: 144104-49-4.mol

Synonyms:144104-49-4;5-(pyridin-3-yl)-1h-indole;5-PYRIDIN-3-YL-1H-INDOLE;1H-Indole, 5-(3-pyridinyl)-;5-Pridin-3-yl-1H-indole;5-(3-Pyridyl)-1H-indole;MLS002206296;SCHEMBL6657347;CHEMBL1435857;DTXSID90566327;HMS2210G03;HMS3330H14;MFCD04114730;AKOS006292395;AB18875;SMR001295114;CS-0334087;A808173;A1-35155

Chemical Property of 5-(Pyridin-3-yl)-1h-indole

Chemical Property:

• Refractive Index: 1.689
• Boiling Point: 420.1±20.0 °C(Predicted)
• PKA: 16.43±0.30(Predicted)
• PSA: 28.68000
• Density: 1.211±0.06 g/cm3(Predicted)
• LogP: 3.22990
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 194.084398327
• Heavy Atom Count: 15
• Complexity: 217

Purity/Quality:

98%min ^*data from raw suppliers

5-pyridin-3-yl-1H-indole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CN=C1)C2=CC3=C(C=C2)NC=C3

Technology Process of 5-(Pyridin-3-yl)-1h-indole

There total 4 articles about 5-(Pyridin-3-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: 91.0%

3-Chloropyridine (626-60-8) + 1H-indole-5-boronic acid (144104-59-6) → 5-(pyridin-3-yl)-1H-indole (144104-49-4)

Guidance literature:

3-Chloropyridine; 1H-indole-5-boronic acid; With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl; In dodecane; butan-1-ol; at 25 ℃; for 0.25h; Glovebox; Inert atmosphere;

With cesiumhydroxide monohydrate; In dodecane; water; butan-1-ol; at 25 ℃; Glovebox; Inert atmosphere;

DOI:10.1002/ejoc.201200918

Reference yield: 90.0%

3-Bromopyridine (626-55-1,163928-56-1) + 5-bromo-1H-indole (10075-50-0) → 5-(pyridin-3-yl)-1H-indole (144104-49-4)

Guidance literature:

3-Bromopyridine; With indium(III) chloride; magnesium; lithium chloride; In tetrahydrofuran; at 25 ℃; for 4h; Schlenk technique; Inert atmosphere;

5-bromo-1H-indole; With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In tetrahydrofuran; at 50 ℃; for 12h; Schlenk technique; Inert atmosphere;

DOI:10.1002/chem.201203795

Reference yield: 82.0%

5-bromo-1H-indole (10075-50-0) + 3-pyridylboronic acid (1692-25-7) → 5-(pyridin-3-yl)-1H-indole (144104-49-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,2-dimethoxyethane; water; at 0 - 20 ℃;

DOI:10.1021/jm500140c

upstream raw materials:

3-Bromopyridine

1H-indole-5-boronic acid

3-Chloropyridine

5-bromo-1H-indole

Refernces

• 1、 Yin, Lina,Hu, Qingzhong,Emmerich, Juliette,Lo, Michael Man-Chu,Metzger, Edward,Ali, Amjad,Hartmann, Rolf W.. "Novel pyridyl- or isoquinolinyl-substituted indolines and indoles as potent and selective aldosterone synthase inhibitors". . p. 5179 - 5189. Retrieved 2014/07/08.
• 2、 Yang, Junfeng,Liu, Sijia,Zheng, Jian-Feng,Zhou, Jianrong. "Room-temperature Suzuki-Miyaura coupling of heteroaryl chlorides and tosylates". supporting information. p. 6248 - 6259,12. Retrieved 2020/09/16.