3-Iodo-7-aza-1H-azaindazole

3-Iodo-7-aza-1H-azaindazole Property

Melting point:

177-179°C

Boiling point:

379.8±22.0 °C(Predicted)

Density 

2.219±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Chloroform, DMSO

form 

Solid

pka

7.96±0.40(Predicted)

color 

Pale Yellow

InChI

InChI=1S/C6H4IN3/c7-5-4-2-1-3-8-6(4)10-9-5/h1-3H,(H,8,9,10)

InChIKey

TYXAGVKIICJXGF-UHFFFAOYSA-N

SMILES

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

Safety

Risk Statements 

36/37/38

Safety Statements 

26-37/39

RIDADR 

UN2811

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-Iodo-7-aza-1H-azaindazole Chemical Properties,Usage,Production

Chemical Properties

Pale Yellow Solid

Uses

3-Iodo-7-aza-1H-azaindazole is used for preparation of azaindazole compounds as CCR1 antagonists.

Synthesis

General procedure for the synthesis of 3-iodo-1H-pyrazolo[3,4-b]pyridine from 1H-pyrazolo[3,4-b]pyridine: 1H-pyrazolo[3,4-b]pyridine (0.50 g, 4.2 mmol), iodine (2.1 g, 8.3 mmol), 3M aqueous NaOH (20 mL) and 1,4-dioxane (20 mL) were added to a reaction flask . The reaction mixture was heated to 55 °C and stirred overnight. Upon completion of the reaction, the organic solvent was evaporated under reduced pressure. Subsequently, acetic acid was added dropwise to the residue and the pH of the solution was adjusted to 5. A yellow solid was precipitated. The precipitate was collected by filtration and dried in air to afford the target product 3-iodo-1H-pyrazolo[3,4-b]pyridine (0.93 g, 90% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3) δ 13.80 (br s, 1H), 8.66 (d, J=4.8 Hz, 1H), 7.88 (d, J=7.2 Hz, 1H), 7.26 (dd, J=7.2, 4.8 Hz, 1H) and MS (ESI) m/z: 246 (M+H)+.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1243 - 1245
[2] Patent: WO2006/130673, 2006, A1. Location in patent: Page/Page column 86
[3] European Journal of Medicinal Chemistry, 2013, vol. 68, p. 361 - 371
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 13, p. 4763 - 4772
[5] Patent: WO2016/97918, 2016, A1. Location in patent: Page/Page column 51-52