5-BROMO-2-CARBOXY-3-METHYLPYRIDINE Chemical Properties

Melting point:

161-163oC

Boiling point:

330.5±42.0 °C(Predicted)

Density 

1.692±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

3.04±0.37(Predicted)

form 

Powder

color 

Off-white

Safety Information

RIDADR 

UN2811

HS Code 

2933399990

5-BROMO-2-CARBOXY-3-METHYLPYRIDINE Usage And Synthesis

Uses

5-Bromo-3-methylpicolinic Acid is used to prepare oxazine derivatives as BACE inhibitors useful in treatment of neurological disorders.

Synthesis

Step B Synthesis of 5-bromo-3-methylpyridine-2-carboxylic acid: 5-bromo-3-methylpyridine-2-carbonitrile (3.9 g, 20 mmol) was dissolved in ethanol (30 mL), followed by the addition of 6.0 M aqueous sodium hydroxide solution (15 mL). The reaction mixture was stirred at 80 °C for 1.5 hours. Upon completion of the reaction, the reaction mixture was concentrated, diluted with water and extracted by partitioning with ethyl acetate (EtOAc). The aqueous phase was acidified to pH 2-3 with hydrochloric acid and the product was subsequently extracted with EtOAc. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the yellow solid product 5-bromo-3-methylpyridine-2-carboxylic acid (4.2 g, 98% yield).

References

[1] Patent: US2013/96144, 2013, A1. Location in patent: Paragraph 0390; 0391
[2] Patent: WO2008/100715, 2008, A1. Location in patent: Page/Page column 33-34

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