4-Bromo-2,6-diethyl-pyridine Chemical Properties

storage temp. 

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

Appearance

Colorless to light yellow Liquid

CAS DataBase Reference

877133-54-5

4-Bromo-2,6-diethyl-pyridine Usage And Synthesis

Uses

4-Bromo-2,6-diethylpyridine is a useful reactant for the synthesis of PF-?00868554 (I)?, an HCV polymerase inhibitor.

Synthesis

The general procedure for the synthesis of 4-bromo-2,6-diethylpyridine using the compound (CAS:1035267-63-0) as starting material was as follows: phosphorus tribromide (2 mL) was slowly added to a solution of 4-bromo-2,6-diethylpyridine 1-oxide (4.3 g, 18.7 mmol) in dichloromethane (30 mL). The reaction mixture was stirred at room temperature for 3 h. The reaction was quenched by careful pouring into ice water. Subsequently, the reaction solution was adjusted to alkaline with 15% sodium hydroxide solution and extracted with ethyl acetate. The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the target product 4-bromo-2,6-diethylpyridine 2.9 g in 72% yield. The product was confirmed by mass spectrometry (ESI), m/z 215 [M + 1]+.

References

[1] Patent: WO2008/76046, 2008, A1. Location in patent: Page/Page column 186-187
[2] Synlett, 2010, # 5, p. 796 - 800