5-BROMO-1H-PYRAZOLO[3,4-B]PYRIDIN-3-YLAMINE Chemical Properties

Boiling point:

429.1±40.0 °C(Predicted)

Density 

1.994

storage temp. 

2-8°C(protect from light)

form 

solid

pka

9.55±0.40(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C6H5BrN4/c7-3-1-4-5(8)10-11-6(4)9-2-3/h1-2H,(H3,8,9,10,11)

InChIKey

SSNUTEUZXZIYTB-UHFFFAOYSA-N

SMILES

C12NN=C(N)C1=CC(Br)=CN=2

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933399990

5-BROMO-1H-PYRAZOLO[3,4-B]PYRIDIN-3-YLAMINE Usage And Synthesis

Uses

3-Amino-5-bromo-1H-pyrazolo[3,4-B]pyridine is an organic intermediate.

Synthesis

General procedure for the synthesis of 3-amino-5-bromo-1H-pyrazolo[3,4-b]pyridine from 5-bromo-2-chloronicotinonitrile: Compound 3 (5-bromo-2-chloronicotinonitrile, 307 mg, 1.4 mmol) was dissolved in ethanol (10 mL) in a microwave reactor tube, followed by the addition of 5 equiv. of hydrazine hydrate (NH2NH2-H2O) to the solution. The reaction mixture was placed in a microwave reactor and radiated at 170 °C for 10 min. Upon completion of the reaction, the solvent was removed by rotary evaporator to afford the target product 3-amino-5-bromo-1H-pyrazolo[3,4-b]pyridine (4) in quantitative yield.

References

[1] Patent: WO2007/59219, 2007, A1. Location in patent: Page/Page column 54-55
[2] Patent: WO2016/26549, 2016, A1. Location in patent: Page/Page column 43
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 20, p. 5578 - 5585
[4] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 9, p. 1577 - 1580
[5] Patent: WO2013/42035, 2013, A1. Location in patent: Page/Page column 17

5-BROMO-1H-PYRAZOLO[3,4-B]PYRIDIN-3-YLAMINE(405224-24-0)Related Product Information

• 3-Aminopyrazine-2-carboxylic acid
• 3-Nitro-1H-pyrazole
• Homopiperazine
• 1H-PYRAZOLO[3,4-B]PYRIDINE
• 5-BROMO-4,6-DIMETHYL-1H-PYRAZOLO[3,4-B]PYRIDIN-3-AMINE
• 5-BROMO-1H-PYRAZOLO[3,4-B]PYRIDIN-3-YLAMINE
• 5-BROMO-1H-PYRAZO[3,4-B]PYRIDINE