5-Iodo-1H-indazole Chemical Properties

Melting point:

156 °C

Boiling point:

358.2±15.0 °C(Predicted)

Density 

2.082±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

Crystalline Powder

pka

12.87±0.40(Predicted)

color 

Yellow to brown to purple

InChI

InChI=1S/C7H5IN2/c8-6-1-2-7-5(3-6)4-9-10-7/h1-4H,(H,9,10)

InChIKey

CGCHCLICSHIAAM-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(I)C=C2)C=N1

Safety Information

HS Code 

29339980

5-Iodo-1H-indazole Usage And Synthesis

Chemical Properties

Solid

Uses

Used as a reactant for the preparation of indazole-pyridine based protein kinase B/Akt inhibitors.

Synthesis

General procedure for the synthesis of 5-iodo-1H-indazole from 5-aminoindazole: 1. a solution of sodium nitrite (2.7 g, 39.1 mmol) in water (40 ml) was slowly added dropwise to a solution of 1-H-indazol-5-amine (5.2 g, 39.1 mmol) in 6 at 0 °C. 2. N hydrochloric acid (73.7 ml) was added to the above mixture at 0°C. 3. the resulting mixture was added slowly and dropwise to a solution of potassium iodide (26.9 g, 162 mmol) in water (60 ml) at 0 °C. 4. The reaction mixture was stirred at room temperature for 3 hours. 5. After completion of the reaction, the reaction mixture was extracted with ethyl acetate (4 x 30 ml). 6. The organic phases were combined and washed sequentially with 10% w/v sodium thiosulfate solution (4 x 30 ml) and brine (2 x 30 ml). 7. The organic phase was dried with anhydrous magnesium sulfate and then concentrated to give a brown solid product. 8. Yield: 8.64 g (90% of theoretical). 9. 9. The structure of the product was confirmed by 3C-NMR (101 MHz, CDCl3, δppm): 84.4, 111.7, 125.6, 129.9, 133.4, 135.4, 139.0.

References

[1] Patent: WO2008/71451, 2008, A1. Location in patent: Page/Page column 47
[2] Patent: WO2014/170020, 2014, A1. Location in patent: Page/Page column 50
[3] Patent: US2009/156590, 2009, A1. Location in patent: Page/Page column 67; 69; 70
[4] Patent: US2012/28984, 2012, A1. Location in patent: Page/Page column 3
[5] Patent: WO2014/202580, 2014, A1. Location in patent: Page/Page column 164

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