2-Bromo-4-methoxypyridine Chemical Properties

Boiling point:

120-121 °C(Press: 10 Torr)

Density 

1.530±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

2.10±0.10(Predicted)

form 

solid

color 

Yellow

Safety Information

HS Code 

2933399990

2-Bromo-4-methoxypyridine Usage And Synthesis

Uses

2-Bromo-4-methoxypyridine acts as a reagent for the synthesis of biarylsulfonamide CCR9 inhibitors for inflammatory bowel diseases.

Synthesis

The general procedure for the synthesis of 2-bromo-4-methoxypyridine from sodium methanol and 2-bromo-4-chloropyridine was as follows: sodium methanol (0.35 g, 6.48 mmol) was added to a solution of 2-bromo-4-chloropyridine (1.0 g, 5.2 mmol) in dimethyl sulfoxide (DMSO, 10 mL). After the addition was completed, the reaction mixture was stirred at 120 °C for 24 hours. After completion of the reaction, the mixture was cooled to room temperature and extracted with ethyl acetate (EtOAc). The organic layers were combined and dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under reduced pressure. Purification of the residue by preparative high performance liquid chromatography (HPLC) gave 2-bromo-4-methoxypyridine (0.25 g, 25% yield) as a colorless oil. The mass spectrometry (MS) electrospray ionization (ESI) calculated value was 189 for C6H6BrNO [M + H]+ and the measured value was 189.

References

[1] Patent: WO2014/74422, 2014, A1. Location in patent: Paragraph 00162

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