1H-Pyrazolo[3,4-b]pyridine,3-methyl-(9CI)

Base Information

• Chemical Name: 1H-Pyrazolo[3,4-b]pyridine,3-methyl-(9CI)
• CAS No.: 116834-96-9
• Molecular Formula: C7H7N3
• Molecular Weight: 133.15100
• Hs Code.: 29331990
• European Community (EC) Number: 844-124-0
• DSSTox Substance ID: DTXSID50441964
• Nikkaji Number: J2.734.420H
• Wikidata: Q72496364
• Mol file: 116834-96-9.mol

Synonyms:3-methyl-2H-pyrazolo[3,4-b]pyridine

Chemical Property of 1H-Pyrazolo[3,4-b]pyridine,3-methyl-(9CI)

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Melting Point: 158-160 °C
• Refractive Index: 1.68
• Boiling Point: 304.3 °C at 760 mmHg
• PKA: 6.52±0.20(Predicted)
• Flash Point: 146.9 °C
• PSA: 41.57000
• Density: 1.273 g/cm³
• LogP: 1.26630
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 133.063997236
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

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

3-Methyl-1H-pyrazolo[3,4-b]pyridine ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C=CC=NC2=NN1

Technology Process of 1H-Pyrazolo[3,4-b]pyridine,3-methyl-(9CI)

There total 12 articles about 1H-Pyrazolo[3,4-b]pyridine,3-methyl-(9CI) 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: 98.0%

3-acetyl-2-chloropyridine (55676-21-6) → 3-methyl-1H-pyrazolo[3,4b]pyridine (116834-96-9)

Guidance literature:

With amino aminoalcohol; at 0 - 90 ℃; for 24h;

DOI:10.1016/j.ejmech.2012.09.034

Reference yield: 69.0%

2-fluoropyridine (372-48-5) + N-Methoxy-N-methylacetamide (78191-00-1) → 3-methyl-1H-pyrazolo[3,4b]pyridine (116834-96-9)

Guidance literature:

2-fluoropyridine; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

N-Methoxy-N-methylacetamide; With hydrazine hydrate; In tetrahydrofuran; hexane; at -78 - 60 ℃; for 1h; Inert atmosphere;

Reference yield:

1-(2-fluoropyridin-3-yl)ethan-1-one (79574-70-2) → 3-methyl-1H-pyrazolo[3,4b]pyridine (116834-96-9)

Guidance literature:

With hydrazine; In ethylene glycol; at 20 - 165 ℃; for 3.5h;

upstream raw materials:

3-acetyl-2-chloropyridine

malonaldehydebis(dimethylacetal)

3-methyl-5-aminopyrazole

methyl-3-pyridylketone

Downstream raw materials:

3-methyl-5-nitropyrazolo<3,4-b>pyridine

1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid

tert-butyl 3-methyl-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

1-(2,4-dichlorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid methyl ester

Refernces

• 1、 -. "3-(3H-IMIDAZO[4,5-B]PYRIDIN-2-YL)-1H-PYRAZOLO[3,4-B]PYRIDINE AND THERAPEUTIC USES THEREOF". Paragraph 1057. . Retrieved 2016/04/20.
• 2、 Jia, Hong,Dai, Guangxiu,Weng, Jianyang,Zhang, Zhulin,Wang, Qing,Zhou, Feng,Jiao, Longxian,Cui, Yumin,Ren, Yongxin,Fan, Shiming,Zhou, Jinghong,Qing, Weiguo,Gu, Yi,Wang, Jian,Sai, Yang,Su, Weiguo. "Discovery of (S)-1-(1-(Imidazo[1,2- a ]pyridin-6-yl)ethyl)-6-(1-methyl-1 H -pyrazol-4-yl)-1 H -[1,2,3]triazolo[4,5- b ]pyrazine (Volitinib) as a Highly Potent and Selective Mesenchymal-Epithelial Transition Factor (c-Met) Inhibitor in Clinical Development for Treatment of Cancer". supporting information. p. 7577 - 7589. Retrieved 2014/12/11.