1-BOC-5-AMINO-INDAZOLE Chemical Properties

Boiling point:

395.3±34.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

solid

pka

3.08±0.10(Predicted)

Appearance

Brown to red Solid

InChI

InChI=1S/C12H15N3O2/c1-12(2,3)17-11(16)15-10-5-4-9(13)6-8(10)7-14-15/h4-7H,13H2,1-3H3

InChIKey

LRSDPIIWOZRHNJ-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)C2=C(C=C(N)C=C2)C=N1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933998090

1-BOC-5-AMINO-INDAZOLE Usage And Synthesis

Uses

tert-Butyl 5-Amino-1H-indazole-1-carboxylate is an intermediate to prepare protein kinase inhibitors.

Synthesis

General procedure for the synthesis of 5-amino-N-tert-butoxycarbonylindazole from 5-nitroindazole: 10% Pd-C catalyst (0.054 g, 0.051 mmol in Pd) and the carbamate from Example 105 (2.647 g, 10.1 mmol) were suspended in 95% ethanol, and the system was degassed under reduced pressure and the reaction was carried out under hydrogen atmosphere. After 23 hours of reaction, the solvent was removed using a rotary evaporator. Ethyl acetate (20 mL) was added to the reaction mixture and after filtration, the filtrate was slowly concentrated on a rotary evaporator to give 2.335 g (100% yield) of brown solid product.LC-MS (ESI) m/z 134 [M-Boc + H]+.

References

[1] Patent: WO2006/135383, 2006, A2. Location in patent: Page/Page column 123-124
[2] Patent: WO2012/146724, 2012, A2
[3] Patent: US2014/57942, 2014, A1
[4] Patent: WO2014/68035, 2014, A1
[5] Asian Journal of Chemistry, 2014, vol. 26, # 22, p. 7539 - 7543

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