1-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Base Information

• Chemical Name: 1-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine
• CAS No.: 348640-02-8
• Molecular Formula: C14H12N2O2S
• Molecular Weight: 272.327
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID70363174
• Nikkaji Number: J2.350.330A
• Wikidata: Q82146764
• ChEMBL ID: CHEMBL1308760
• Mol file: 348640-02-8.mol

Synonyms:348640-02-8;1-Tosyl-1H-pyrrolo[2,3-b]pyridine;1-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine;1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridine;1H-PYRROLO[2,3-B]PYRIDINE, 1-[(4-METHYLPHENYL)SULFONYL]-;1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine;MLS000331284;n-tosyl-7-azaindole;Oprea1_669808;SCHEMBL1714526;1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine;CHEMBL1308760;DTXSID70363174;HMS2364F07;BCP14332;CS-B0530;YNA64002;MFCD02083277;AKOS005075991;AB10664;CCG-277879;10P-414S;SMR000168748;W16211;A874840;AN-584/43363401;1-[(4-methylphenyl)sulphonyl]-1H-pyrrolo[2,3-b]pyridine;1H-Pyrrolo[2,3-b]pyridine,1-[(4-methylphenyl)sulfonyl]-;1-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine, AldrichCPR

Chemical Property of 1-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Chemical Property:

• Vapor Pressure: 5.11E-09mmHg at 25°C
• Melting Point: 132-133℃
• Boiling Point: 470.3°C at 760 mmHg
• Flash Point: 238.2°C
• PSA: 60.34000
• Density: 1.31g/cm³
• LogP: 3.66250
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 272.06194880
• Heavy Atom Count: 19
• Complexity: 410

Purity/Quality:

97% ^*data from raw suppliers

1-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2C=CC3=C2N=CC=C3

Technology Process of 1-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

There total 3 articles about 1-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine 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: 93.0%

7-Azaindole (271-63-6) + p-toluenesulfonyl chloride (98-59-9) → 1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine (348640-02-8)

Guidance literature:

7-Azaindole; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 0.5h;

p-toluenesulfonyl chloride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃;

Reference yield: 31.0%

1-(4-toluenesulfonyl)-1H-1,2,4-triazole (13578-51-3) + 1H-Pyrrolo[2,3-b]pyridine-7-oxide (55052-24-9) → 1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine (348640-02-8) + 6-(1,2,4-triazol-2-yl)-7-azaindole (935466-64-1) + C16H13N5O2S (1219601-43-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; at 90 ℃; for 2h; Inert atmosphere; Neat (no solvent);

DOI:10.1021/jo1001017

Reference yield:

1-(p-tolylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine + (PPh3)(3,5-(CF3)2Ph)Pd(CF3)Br(18-crown-6)K?1/2THF → 1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine (348640-02-8) + 5-((3,5-bis(trifluoromethyl)phenyl)difluoromethyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Guidance literature:

(PPh₃)(3,5-(CF₃)₂Ph)Pd(CF₃)Br(18-crown-6)K?1/2THF; With tris(pentafluorophenyl)borate; In tetrahydrofuran; at 25 ℃; for 0.0833333h;

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine; With tetramethylammonium fluoride; triphenylphosphine; In tetrahydrofuran; at 80 ℃; for 16h; Overall yield = 27 percent; Overall yield = 14.3 mg;

DOI:10.1021/jacs.0c09505

upstream raw materials:

7-Azaindole

p-toluenesulfonyl chloride

1-(4-toluenesulfonyl)-1H-1,2,4-triazole

1H-Pyrrolo[2,3-b]pyridine-7-oxide

Downstream raw materials:

2-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine

2-(5-methoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

2-(5,7-dimethoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

2-(5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine