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

Base Information

• Chemical Name: 1H-pyrazolo[3,4-b]pyridine
• CAS No.: 271-73-8
• Molecular Formula: C6H5N3
• Molecular Weight: 119.126
• Hs Code.: 29331990
• European Community (EC) Number: 692-659-1
• DSSTox Substance ID: DTXSID20949861
• Nikkaji Number: J627.996A
• Wikidata: Q72503505
• Mol file: 271-73-8.mol

Synonyms:1H-pyrazolo(3,4-b)pyridine

Chemical Property of 1H-pyrazolo[3,4-b]pyridine

Chemical Property:

• Appearance/Colour: Pale orange solid
• Vapor Pressure: 0.003mmHg at 25°C
• Melting Point: 99-101 °C
• Refractive Index: 1.715
• Boiling Point: 294.466 °C at 760 mmHg
• PKA: 5.92±0.20(Predicted)
• Flash Point: 145.716 °C
• PSA: 41.57000
• Density: 1.349 g/cm³
• LogP: 0.95790
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 119.048347172
• Heavy Atom Count: 9
• Complexity: 105

Purity/Quality:

99% ^*data from raw suppliers

7-Azaindazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-20/21/22
• Safety Statements: 36/37

MSDS Files:

Useful:

• Canonical SMILES: C1=CC2=C(NN=C2)N=C1
• Uses: A pyrazole derivative as kinase inhibitors.

Technology Process of 1H-pyrazolo[3,4-b]pyridine

There total 14 articles about 1H-pyrazolo[3,4-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: 98.0%

2-chloro-3-carbaldehydepyridine (36404-88-3) → 1H-Pyrazolo[3,4-b]pyridine (271-73-8)

Guidance literature:

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

DOI:10.1016/j.ejmech.2012.09.034

Reference yield: 93.0%

3-Diazapyrazolo<3,4-b>pyridine (63682-42-8) → 1H-Pyrazolo[3,4-b]pyridine (271-73-8) + 3-Chloro-1H-pyrazolo<3,4-b>pyridine (117007-51-9)

Guidance literature:

With hydrogenchloride; for 0.583333h; Heating;

DOI:10.1007/BF00809212

Reference yield: 90.0%

2-fluoropyridine-3-carboxaldehyde (36404-90-7) → 1H-Pyrazolo[3,4-b]pyridine (271-73-8)

Guidance literature:

With hydrazine hydrate; In ethanol; at 80 ℃; for 1h;

upstream raw materials:

2-chloro-3-carbaldehydepyridine

1‐benzyl‐1H‐pyrazolo[3,4‐b]pyridine

1-ethyl-1H-pyrazolo<3,4-b>pyridine

3-Diazapyrazolo<3,4-b>pyridine

Downstream raw materials:

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-pyrazolo[3,4-b]pyridine

N-((1R,3S)-3-((5-fluoro-2-(1-trityl-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-yl)amino)cyclohexyl)-1-methyl-1H-imidazole-4-carboxamide

N-((1R,3S)-3-((5-fluoro-2-(1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-yl)amino)cyclohexyl)-1-methyl-1H-imidazole-4-carboxamide

3-bromo-1-trityl-pyrazolo[3,4-b]pyridine

Refernces

• 1、 Hatt,Vass. "-". . p. 293. Retrieved 1966.
• 2、 Rekowski, Szymon P.,Kroener, Bettina K.,Kathuria, Deepika,Wani, Aabid A.,Chourasiya, Sumit S.,Conrad, Jürgen,Bharatam, Prasad V.,Frey, Wolfgang,Beifuss, Uwe. "A novel copper-catalyzed, hydrazine-free synthesis of N-1 unsubstituted 1H-indazoles using stable guanylhydrazone salts as substrates". . . Retrieved 2021/06/12.
• 3、 Faarasse, Soukaina,El Kazzouli, Sa?d,Naas, Mohammed,Jouha, Jabrane,Suzenet, Franck,Guillaumet, Gérald. ""On Water" Direct C-3 Arylation of 2H-Pyrazolo[3,4-b]pyridines". . p. 12300 - 12306. Retrieved 2017/12/08.