6-chloro-1H-pyrazolo[3,4-b]pyridine Chemical Properties

Boiling point:

262℃

Density 

1.61

Flash point:

113℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

5.20±0.40(Predicted)

form 

solid

color 

Yellow-brown

InChI

InChI=1S/C6H4ClN3/c7-5-2-1-4-3-8-10-6(4)9-5/h1-3H,(H,8,9,10)

InChIKey

NWYLBGYCSAJFCB-UHFFFAOYSA-N

SMILES

C12NN=CC1=CC=C(Cl)N=2

Safety Information

HS Code 

2933399990

6-chloro-1H-pyrazolo[3,4-b]pyridine Usage And Synthesis

Synthesis

GENERAL STEPS: To a solution of tetrahydrofuran (THF, 30 mL) containing 6-chloro-2-fluoropyridine-3-carbaldehyde (4.0 g, 25.1 mmol) was added hydrazine hydrate (2.515 g, 56.3 mmol). The reaction mixture was heated at 60 °C with stirring for 5 hours. Upon completion of the reaction, the mixture was concentrated and quenched with ice water. The solid formed was collected by filtration and dried under vacuum to afford 6-chloro-1hydro-pyrazolo[3,4-B]pyridine (3.5 g, 92% yield). The product was characterized by 1H NMR (DMSO-d6, 300 MHz): δ 13.8 (s, 1H), 8.32-8.29 (d, 1H), 8.20 (s, 1H), 7.27-7.24 (d, 1H). the LCMS analysis showed a purity of 89.96%, m/z = 153.9 (M + 1).

References

[1] Patent: WO2017/9798, 2017, A1. Location in patent: Page/Page column 66

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