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

Base Information

• Chemical Name: 4-methyl-1H-pyrrolo[2,3-b]pyridine
• CAS No.: 824-24-8
• Molecular Formula: C8H8 N2
• Molecular Weight: 132.165
• Hs Code.: 2933990090
• European Community (EC) Number: 835-336-4
• DSSTox Substance ID: DTXSID70421369
• Mol file: 824-24-8.mol

Synonyms:4-Methyl-7-azaindole;4-methyl-1H-pyrrolo[2,3-b]pyridine;824-24-8;MFCD00956196;SCHEMBL91443;SCHEMBL23840514;AMY9686;DTXSID70421369;KEBIZMQVCXHCGN-UHFFFAOYSA-N;BCP04307;AKOS006274006;DS-5690;PB19900;CS-0004137;FT-0684899;EN300-97046;A840331;J-515694;Z1198155764

Chemical Property of 4-methyl-1H-pyrrolo[2,3-b]pyridine

Chemical Property:

• Vapor Pressure: 0.00423mmHg at 25°C
• Melting Point: 125-126 ºC
• Refractive Index: 1.666
• Boiling Point: 287.7°C at 760 mmHg
• PKA: 7.94±0.20(Predicted)
• Flash Point: 128.8°C
• PSA: 28.68000
• Density: 1.17
• LogP: 1.87130
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 132.068748264
• Heavy Atom Count: 10
• Complexity: 124

Purity/Quality:

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

4-methyl-1H-pyrrolo[2,3-b]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C=CNC2=NC=C1

Technology Process of 4-methyl-1H-pyrrolo[2,3-b]pyridine

There total 1 articles about 4-methyl-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: 89.0%

methylmagnesium bromide (75-16-1) + 4-chloro-7-azaindole (55052-28-3) → 4-methyl-1H-pyrrolo[2,3-b]pyridine (824-24-8)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In diethyl ether; toluene; at 30 - 80 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.8b00392

Reference yield: 65.0%

4-methyl-1H-pyrrolo[2,3-b]pyridine (824-24-8) + benzenesulfonyl chloride (98-09-9) → 4-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (1227270-73-6)

Guidance literature:

4-methyl-1H-pyrrolo[2,3-b]pyridine; With tetrabutylammomium bromide; potassium hydroxide; In dichloromethane; water; at 28 ℃; for 0.166667h;

benzenesulfonyl chloride; In dichloromethane; water; at 30 ℃; for 4h;

DOI:10.1021/acs.jmedchem.8b00392

Reference yield: 41.4%

4-methyl-1H-pyrrolo[2,3-b]pyridine (824-24-8) + p-toluenesulfonyl chloride (98-59-9) → 4-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

upstream raw materials:

methylmagnesium bromide

4-chloro-7-azaindole

Downstream raw materials:

4-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

4-methyl-5-nitro-1H-pyrrolo[2,3-b]pyridine

Refernces

• 1、 Schnute, Mark E.,Wennerstal, Mattias,Alley, Jennifer,Bengtsson, Martin,Blinn, James R.,Bolten, Charles W.,Braden, Timothy,Bonn, Tomas,Carlsson, Bo,Caspers, Nicole,Chen, Ming,Choi, Chulho,Collis, Leon P.,Crouse, Kimberly,F?rnegardh, Mathias,Fennell, Kimberly F.,Fish, Susan,Flick, Andrew C.,Goos-Nilsson, Annika,Gullberg, Hjalmar,Harris, Peter K.,Heasley, Steven E.,Hegen, Martin,Hromockyj, Alexander E.,Hu, Xiao,Husman, Bolette,Janosik, Tomasz,Jones, Peter,Kaila, Neelu,Kallin, Elisabet,Kauppi, Bj?rn,Kiefer, James R.,Knafels, John,Koehler, Konrad,Kruger, Lars,Kurumbail, Ravi G.,Kyne, Robert E.,Li, Wei,L?fstedt, Joakim,Long, Scott A.,Menard, Carol A.,Mente, Scot,Messing, Dean,Meyers, Marvin J.,Napierata, Lee,N?teberg, Daniel,Nuhant, Philippe,Pelc, Matthew J.,Prinsen, Michael J.,Rh?nnstad, Patrik,Backstr?m-Rydin, Eva,Sandberg, Johnny,Sandstr?m, Maria,Shah, Falgun,Sj?berg, Maria,Sundell, Aron,Taylor, Alexandria P.,Thorarensen, Atli,Trujillo, John I.,Trzupek, John D.,Unwalla, Ray,Vajdos, Felix F.,Weinberg, Robin A.,Wood, David C.,Xing, Li,Zamaratski, Edouard,Zapf, Christoph W.,Zhao, Yajuan,Wilhelmsson, Anna,Berstein, Gabriel. "Discovery of 3-Cyano- N-(3-(1-isobutyrylpiperidin-4-yl)-1-methyl-4-(trifluoromethyl)-1 H-pyrrolo[2,3- b]pyridin-5-yl)benzamide: A Potent, Selective, and Orally Bioavailable Retinoic Acid Receptor-Related Orphan Receptor C2 Inverse Agonist". . p. 10415 - 10439. Retrieved 2018/09/20.