5-BROMO-7-INDAZOLECARBOXYLIC ACID METHYL ESTER Chemical Properties

Boiling point:

395.9±22.0 °C(Predicted)

Density 

1.709±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

10.67±0.40(Predicted)

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C9H7BrN2O2/c1-14-9(13)7-3-6(10)2-5-4-11-12-8(5)7/h2-4H,1H3,(H,11,12)

InChIKey

QQXHHJBRURQNLO-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(Br)C=C2C(OC)=O)C=N1

Safety Information

RIDADR 

2811

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2933998090

5-BROMO-7-INDAZOLECARBOXYLIC ACID METHYL ESTER Usage And Synthesis

Synthesis

Methyl 2-amino-5-bromo-3-methylbenzoate (19-S3, 10.9 g, 44.7 mmol) and potassium acetate (AcOK, 1.32 g, 13.41 mmol) were dissolved in dichloromethane (CH2Cl2, 50 mL) under nitrogen protection and cooled to 0 °C. Acetic anhydride (Ac2O, 10.6 g, 103 mmol) was added slowly and the reaction mixture was stirred at room temperature for 1 hour. Subsequently, the mixture was heated to 60 °C and tert-butyl nitrite (t-BuONO, 10.2 g, 98.3 mmol) was added. The resulting mixture was continued to be stirred at 60 °C for 4 hours. After completion of the reaction, it was cooled to room temperature, the reaction was quenched with saturated aqueous sodium bicarbonate (NaHCO3) and extracted with ethyl acetate (EtOAc). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to give the crude product. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=100:0 to 10:1) to afford methyl 5-bromo-1H-indazole-7-carboxylate (19-S4, 8.0 g, 70.5% yield) as a yellow solid. lc-MS (ESI) m/z: 255 (M+H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 11, p. 2578 - 2581
[2] Patent: WO2018/160889, 2018, A1. Location in patent: Page/Page column 474; 475
[3] Patent: WO2015/157093, 2015, A1. Location in patent: Paragraph 0394
[4] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 3, p. 1156 - 1162
[5] Patent: WO2008/65508, 2008, A1

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