1H-Pyrazolo[3,4-b]pyridine-3-carboxylicacid(9CI) Chemical Properties

Melting point:

265-270℃ (DEC.)

Boiling point:

391.1±25.0 °C(Predicted)

Density 

1.68

storage temp. 

2-8°C

pka

8.83±0.20(Predicted)

Appearance

Light yellow to brown Solid

InChI

InChI=1S/C7H5N3O2/c11-7(12)5-4-2-1-3-8-6(4)10-9-5/h1-3H,(H,11,12)(H,8,9,10)

InChIKey

UFKAACYLUOQSFH-UHFFFAOYSA-N

SMILES

C12NN=C(C(O)=O)C1=CC=CN=2

Safety Information

Risk Statements 

20/21/22

Safety Statements 

24/25-36/37

HS Code 

29339900

1H-Pyrazolo[3,4-b]pyridine-3-carboxylicacid(9CI) Usage And Synthesis

Chemical Properties

Light yellow solid

Uses

1h-Pyrazolo[3,4-B]Pyridine-3-Carboxylic Acid is a useful research chemical.

Synthesis

Step 4: To an aqueous solution (20 mL) containing NaOH (0.88 g, 22 mmol) was added 3-methyl-1H-pyrazolo[3,4-b]pyridine (IV) (0.4 g, 3 mmol). The suspension was heated at 80°C until a clarified solution was formed. Subsequently, an aqueous solution (180 mL) of KMnO4 (1.73 g, 11 mmol) was added slowly over a period of 2 hours while keeping the solution heated at 80°C. The solution was heated at 90°C for 2 hours. The reaction mixture was continued to be heated at 90°C for 2 hours until the complete disappearance of the feedstock was confirmed by thin layer chromatography (TLC). The solution was cooled to 70°C and filtered through a diatomaceous earth pad. The solids were washed with boiling water. The filtrates were combined and cooled to 0°C and acidified with concentrated HCl to pH=2. The acidified solution was extracted with n-butanol (2 x 10 mL). The n-butanol layer was concentrated under reduced pressure to give a white residue. The residue was dissolved in dichloromethane (DCM), a minimum amount of methanol (MeOH) was added to aid solubilization, and then filtered. The filtrate was concentrated to afford 1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (V) as a white solid (390 mg, 2.39 mmol, 81% yield).1H NMR (CDCl3) δ ppm: 7.37 (dd, J = 8.10, 4.52 Hz, 1H), 8.47 (dd, J = 7.54, 1.88 Hz, 1H), 8.62 (dd, J = 7.54, 1.88 Hz, 1H), 8.63 (dd, J = 7.54, 1.88 Hz, 1H). 8.62 (dd, J = 4.52, 1.32 Hz, 1H), 14.37 (brs, 1H).

References

[1] Patent: WO2011/84486, 2011, A1. Location in patent: Page/Page column 106; 111-112
[2] Patent: US2013/296302, 2013, A1. Location in patent: Paragraph 0496
[3] Patent: US2016/68550, 2016, A1. Location in patent: Paragraph 1058
[4] Patent: WO2016/40193, 2016, A1. Location in patent: Paragraph 0705
[5] Canadian Journal of Chemistry, 1988, vol. 66, # 3, p. 420-428

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