7-CHLORO-5-METHYL-1H-PYRAZOLO[4,3-B]PYRIDINE Chemical Properties

Boiling point:

307.3±37.0 °C(Predicted)

Density 

1.438±0.06 g/cm3(Predicted)

storage temp. 

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

pka

9.09±0.40(Predicted)

Appearance

Light brown to brown Solid

InChI

InChI=1S/C7H6ClN3/c1-4-2-5(8)7-6(10-4)3-9-11-7/h2-3H,1H3,(H,9,11)

InChIKey

GTYZRPHAMFVUEE-UHFFFAOYSA-N

SMILES

C12C=NNC1=C(Cl)C=C(C)N=2

Safety Information

HS Code 

2933399990

7-CHLORO-5-METHYL-1H-PYRAZOLO[4,3-B]PYRIDINE Usage And Synthesis

Synthesis

Step 1: 5-methyl-1H-pyrazolo[4,3-b]pyridin-7-ol (4.58 g, 30.7 mmol) was dissolved in phosphorochloridic acid (30 mL) and the reaction was heated at 110 °C for 30 min. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently slowly poured into ice water. The pH of the mixture was adjusted with 6N NaOH solution to 5. The precipitated solid product was collected by filtration. The mother liquor layer was extracted with ethyl acetate (3 x 250 mL). The above solids were dissolved in the combined organic phases, washed with brine solution (1 x 250 mL), dried over anhydrous sodium sulfate, filtered and concentrated. Purification of the concentrate by short silica gel column chromatography afforded 7-chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine (Compound Ie) as a light yellow solid (4.50 g, 26.8 mmol, 87% yield).GC/MS analysis: m/z = 167 (100%); LC/MS analysis: [M + H]+ = 168.

References

[1] Journal of Medicinal Chemistry, 2005, vol. 48, # 18, p. 5780 - 5793
[2] Patent: WO2006/44821, 2006, A1. Location in patent: Page/Page column 23-24

7-CHLORO-5-METHYL-1H-PYRAZOLO[4,3-B]PYRIDINE(94220-38-9)Related Product Information

• 3-BROMO-7-CHLORO-5-METHYL-1H-PYRAZOLO[4,3-B]PYRIDINE
• 7-CHLORO-5-METHYL-1H-PYRAZOLO[4,3-B]PYRIDINE