3-BROMO-PYRAZOLO[1,5-A]PYRIDINE Chemical Properties

Melting point:

55 °C(Solv: ligroine (8032-32-4))

Density 

1.69±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

0.56±0.30(Predicted)

Appearance

Off-white to gray Solid

InChI

InChI=1S/C7H5BrN2/c8-6-5-9-10-4-2-1-3-7(6)10/h1-5H

InChIKey

NMPZEHJXHWTZNI-UHFFFAOYSA-N

SMILES

C12=C(Br)C=NN1C=CC=C2

Safety Information

HS Code 

2933998090

3-BROMO-PYRAZOLO[1,5-A]PYRIDINE Usage And Synthesis

Uses

3-Bromopyrazolo[1,5-a]pyridine is used as a pharmaceutical intermediate compound for the preparation of Hpk1 antagonists.

Synthesis

The general procedure for the synthesis of 3-bromopyrazolo[1,5-a]pyridine-3-carboxylic acid from pyrazolo[1,5-a]pyridine was as follows: N-bromosuccinimide (3.06 g, 17.22 mmol) and sodium bicarbonate (4.34 g, 51.66 mmol) were sequentially added to a N,N-dimethylformamide (40 mL) solution of pyrazolo[1,5-a]pyridine-3-carboxylic acid (2.81 g, 17.22 mmol) in a solution of N,N-dimethylformamide (40 mL). The reaction mixture was stirred at room temperature for 4 h and then poured into water (100 mL). The resulting suspension was extracted twice with ethyl acetate and the organic layers were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by concentration under reduced pressure. The crude product was purified by fast column chromatography (eluent: hexane/ethyl acetate = 8:2) to afford the target product 3-bromopyrazolo[1,5-a]pyridine (2.58 g, 76% yield). Mass spectrum (LRMS) showed m/z: 197 ([M+1]+). 1H-NMR (250 MHz, CDCl3) δ: 6.8 (t, 1H), 7.2 (t, 1H), 7.5 (d, 1H), 7.9 (s, 1H), 8.4 (d, 1H).

References

[1] Patent: WO2011/101161, 2011, A1. Location in patent: Page/Page column 99

3-BROMO-PYRAZOLO[1,5-A]PYRIDINE(5910-12-3)Related Product Information

• 3-bromoH-pyrazolo[1,5-a]pyridine-2-carboxylic acid
• 3-BROMO-PYRAZOLO[1,5-A]PYRIDINE
• Pyrazolo[1,5-a]pyridine
• 3-BROMO-2-(4-FLUOROPHENYL)-6-(TRIFLUOROMETHYL)PYRAZOLO[1,5-A]PYRIDINE