1H-INDAZOLE-6-CARBOXYLIC ACID,3-IODO-,METHYL ESTER Chemical Properties

Boiling point:

421.4±25.0 °C(Predicted)

Density 

1.948±0.06 g/cm3(Predicted)

storage temp. 

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

pka

10.47±0.40(Predicted)

form 

solid

color 

Beige

InChIKey

VSXHXVGWOSYULI-UHFFFAOYSA-N

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

WGK Germany 

3

HS Code 

2933998090

1H-INDAZOLE-6-CARBOXYLIC ACID,3-IODO-,METHYL ESTER Usage And Synthesis

Application

3-Iodoindazole-6-carboxylic acid methyl ester is an indazole compound that is widely used in the pharmaceutical and chemical industries.

Synthesis

General procedure for the synthesis of methyl 3-iodoindazole-6-carboxylate from methyl 1H-indazole-6-carboxylate: To a solution of methyl 1H-indazole-6-carboxylate (2.5 g, 14.2 mmol) in DMF (30 mL) was added in batches of KOH (1.8 g, 31.9 mmol), followed by the addition of iodine (5.4 g, 21.3 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the mixture was poured into ice water and extracted twice with EtOAc. The organic phases were combined, washed sequentially with 5% Na2S2O4 aqueous solution and brine, dried and concentrated to dryness to afford methyl 3-iodoindazole-6-carboxylate (4.0 g, 93.3% yield) as a yellow solid, which could be used in the next reaction without further purification.LC/MS (ESI) m/z: 303 (M + H)+.

References

[1] Patent: WO2018/160891, 2018, A1. Location in patent: Page/Page column 537-540
[2] Patent: US2012/108619, 2012, A1. Location in patent: Page/Page column 32
[3] Patent: US2012/270893, 2012, A1. Location in patent: Page/Page column 22-23
[4] Patent: WO2014/26328, 2014, A1. Location in patent: Page/Page column 41
[5] Patent: WO2014/28597, 2014, A2. Location in patent: Page/Page column 57

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