6-METHOXY-3-METHYL-1H-INDAZOLE Chemical Properties

Melting point:

168-169 °C

Boiling point:

323.0±22.0 °C(Predicted)

Density 

1.198±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

14.68±0.40(Predicted)

Safety Information

HS Code 

2933998090

6-METHOXY-3-METHYL-1H-INDAZOLE Usage And Synthesis

Uses

6-Methoxy-3-methyl-1H-indazole is a pharmaceutical intermediate compound that is used in the preparation of EGFR inhibitors.

Synthesis

General procedure for the synthesis of 6-methoxy-3-methyl-1H-indazole from 2-fluoro-4-methoxyacetophenone: 1-(2-fluoro-4-methoxyphenyl)ethan-1-one (2 g, 11.9 mmol) was dissolved in a mixture of 5 mL of hydrazine hydrate (85%) and N-methylpyrrolidone (NMP, 15 mL). The reaction mixture was stirred at 120°C for 24 hours. After completion of the reaction, the product was purified by column chromatography to afford 6-methoxy-3-methyl-1H-indazole (1.5 g, 78% yield).

References

[1] Patent: WO2016/8590, 2016, A1. Location in patent: Page/Page column 50
[2] Patent: EP3205650, 2017, A1. Location in patent: Paragraph 0106; 0365; 0366
[3] Patent: US6956036, 2005, B1
[4] Patent: US6552062, 2003, B1
[5] Patent: WO2009/144554, 2009, A1. Location in patent: Page/Page column 49-50

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