1-(Benzenesulfonyl)-2-(pyridin-2-yl)-1H-indole

Base Information

• Chemical Name: 1-(Benzenesulfonyl)-2-(pyridin-2-yl)-1H-indole
• CAS No.: 73282-12-9
• Molecular Formula: C19H14N2O2S
• Molecular Weight: 334.398
• DSSTox Substance ID: DTXSID40502851
• Nikkaji Number: J754.043D
• Wikidata: Q82356218
• Mol file: 73282-12-9.mol

Synonyms:73282-12-9;1-(Benzenesulfonyl)-2-(pyridin-2-yl)-1H-indole;DTXSID40502851

Chemical Property of 1-(Benzenesulfonyl)-2-(pyridin-2-yl)-1H-indole

Chemical Property:

• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 334.07759887
• Heavy Atom Count: 24
• Complexity: 524

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)S(=O)(=O)N2C3=CC=CC=C3C=C2C4=CC=CC=N4

Technology Process of 1-(Benzenesulfonyl)-2-(pyridin-2-yl)-1H-indole

There total 13 articles about 1-(Benzenesulfonyl)-2-(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: 100.0%

2-bromo-pyridine (109-04-6) + 2-(trimethylstannyl)-N-(benzenesulfonyl)indole → 1-phenylsulfonyl-2-(pyridin-2-yl)-1H-indole (73282-12-9)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; at 100 ℃; for 6h;

DOI:10.1016/j.tet.2008.09.101

Reference yield: 97.0%

2-bromo-pyridine (109-04-6) + 1-benzenesulfonylindole (40899-71-6) → 1-phenylsulfonyl-2-(pyridin-2-yl)-1H-indole (73282-12-9)

Guidance literature:

1-benzenesulfonylindole; With lithium diisopropyl amide; In tetrahydrofuran; cyclohexane; at 0 ℃; for 0.5h;

With zinc(II) chloride; In tetrahydrofuran; cyclohexane; at 20 ℃; for 0.5h;

2-bromo-pyridine; With bis-triphenylphosphine-palladium(II) chloride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; cyclohexane; for 6h; Further stages.; Heating;

DOI:10.1021/ja9944249

Reference yield: 74.0%

2-(2-pyridinyl)-1H-indole (13228-40-5) + benzenesulfonyl chloride (98-09-9) → 1-phenylsulfonyl-2-(pyridin-2-yl)-1H-indole (73282-12-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 10 ℃;

DOI:10.1016/j.tet.2006.03.085

upstream raw materials:

2-chloropyridine

2-bromo-pyridine

2-iodo-1-(phenylsulfonyl)-1H-indole

2-(2-pyridinyl)-1H-indole

Downstream raw materials:

1-(1-Benzenesulfonyl-2-pyridin-2-yl-1H-indol-3-yl)-ethanol

indolo[2,3-a]quinolizine

1-benzenesulfonyl-2-(pyridin-N-oxide-2-yl)-1H-indole

1,2,3,4,6,7,12,12b-octahydroindolo(2,3-a)quinolizine

Refernces

• 1、 Lipińska, Teodozja M.. "Total synthesis of new indolo[2,3-a]quinolizine alkaloids sempervirine type, potential pharmaceuticals". . p. 5736 - 5747. Retrieved 2007/10/03.
• 2、 Amat, Mercedes,Hadida, Sabine,Pshenichnyi, Grigorii,Bosch, Joan. "Palladium(0)-catalyzed heteroarylation of 2- and 3-indolylzinc derivatives. An efficient general method for the preparation of (2-pyridyl)indoles and their application to indole alkaloid synthesis". . p. 3158 - 3175. Retrieved 2007/10/03.