3-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

Base Information

• Chemical Name: 3-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine
• CAS No.: 744209-37-8
• Molecular Formula: C14H11BrN2O2S
• Molecular Weight: 351.224
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40457099
• Wikidata: Q82279806
• Mol file: 744209-37-8.mol

Synonyms:744209-37-8;3-BROMO-2-METHYL-1-(PHENYLSULFONYL)-1H-PYRROLO[2,3-B]PYRIDINE;3-broMo-2-Methyl-1-(phenylsulfonyl)-1H-pyrrolo[2.3-b]pyridine;1-(benzenesulfonyl)-3-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine;1-(BENZENESULFONYL)-3-BROMO-2-METHYLPYRROLO[2,3-B]PYRIDINE;MFCD13191649;SCHEMBL15635129;DTXSID40457099;FALZHLDFXNLJAR-UHFFFAOYSA-N;AMY12347;AKOS025290467;PB11072;AS-42051;SY098035;CS-0004768;3-bromo-2-methyl-1-(benzenesulfonyl)-7-azaindole;3-Bromo-2-methyl-1-(phenylsulfonyl)-7-azaindole;3-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine, AldrichCPR

Chemical Property of 3-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

Chemical Property:

• PSA: 60.34000
• LogP: 4.42500
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 349.97246
• Heavy Atom Count: 20
• Complexity: 445

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-(Benzenesulfonyl)-3-bromo-2-methylpyrrolo[2,3-b]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C(N1S(=O)(=O)C3=CC=CC=C3)N=CC=C2)Br

Technology Process of 3-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

There total 4 articles about 3-Bromo-2-methyl-1-(phenylsulfonyl)-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: 83.0%

1-benzenesulfonyl-2-methyl-1H-pyrrolo[2,3-b]pyridine (189089-83-6) → 3-bromo-2-methyl-1-phenylsulfonylpyrrolo[2,3-b]pyridine (744209-37-8)

Guidance literature:

With tetrachloromethane; N-Bromosuccinimide; at 20 ℃; for 12h;

DOI:10.1016/j.dyepig.2014.03.003

Reference yield:

7-Azaindole (271-63-6) → 3-bromo-2-methyl-1-phenylsulfonylpyrrolo[2,3-b]pyridine (744209-37-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 87 percent / benzyltriethylammonium chloride; NaOH / CH₂Cl₂ / 0 - 20 °C

2.1: LDA / tetrahydrofuran / 0.67 h / -30 °C

2.2: 96 percent / tetrahydrofuran / 3 h / 20 °C

3.1: 67 percent / NBS / CCl₄ / 12 h / 20 °C

With sodium hydroxide; N-Bromosuccinimide; N-benzyl-N,N,N-triethylammonium chloride; lithium diisopropyl amide; In tetrahydrofuran; tetrachloromethane; dichloromethane;

DOI:10.1021/jo0358168

Reference yield:

benzenesulfonyl chloride (98-09-9) → 3-bromo-2-methyl-1-phenylsulfonylpyrrolo[2,3-b]pyridine (744209-37-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / dichloromethane / 0.17 h / -0.16 °C

1.2: 12.33 h / 0 - 20 °C

2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 0.5 h / -25.16 °C / Inert atmosphere

2.2: 10 h / 20 - 25 °C / Inert atmosphere

3.1: N-Bromosuccinimide; tetrachloromethane / 12 h / 20 °C

With tetrachloromethane; N-Bromosuccinimide; N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/j.dyepig.2014.03.003

upstream raw materials:

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

7-Azaindole

benzenesulfonyl chloride

Downstream raw materials:

1-(1,2-dimethyl-7-azaindol-3-yl)-2-[2-methyl-5-(4-trifluoromethylphenyl)-3-thienyl]perfluorocyclopentene

1-(1,2-dimethyl-7-azaindol-3-yl)-2-[2-methyl-5-(4-fluorophenyl)-3-thienyl]perfluorocyclopentene

1-(1,2-dimethyl-7-azaindole-3-yl)-2-(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene

1-(1,2-dimethyl-7-azaindol-3-yl)-2-[2-methyl-5-(4-methylphenyl)-3-thienyl]perfluorocyclopentene

Refernces

• 1、 Sun, Zhiyuan,Li, Hui,Liu, Gang,Fan, Congbin,Pu, Shouzhi. "Photochromism of new unsymmetrical diarylethenes based on the hybrid of azaindole and thiophene moieties". . p. 94 - 104. Retrieved 2014/04/17.
• 2、 Mendiola, Javier,Baeza, Alejandro,Alvarez-Builla, Julio,Vaquero, Juan J.. "Reaction of bromomethylazoles and tosylmethyl isocyanide. A novel heterocyclization method for the synthesis of the core of marine alkaloids variolins and related azolopyrimidines". . p. 4974 - 4983. Retrieved 2007/10/03.