Reacción #86184

Ecuación de reacción

Diisopropylamine

N-Butyllithium

Hexane

2-bromo-6-fluoro-pyridine

Iodomethane

→

6-bromo-2-fluoro-3-methyl-pyridine

Rendimiento 55.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to −78° C
2. 2
   workup.STIRRINGThe mixture was stirred at −78° C. for 3 h
3. 3
   Temperaturato warm to room temperature
4. 4
   workup.STIRRINGwith stirring for 1 hour
5. 5
   OtroThe reaction was quenched with water (˜50 mL)
6. 6
   workup.STIRRINGstirred overnight
7. 7
   OtroThe layers were separated
8. 8
   ConcentraciónThe organic layer was concentrated
9. 9
   Otrothe residue was purified on silica
10. 10
    Lavadoeluted with 0 to 5% EtOAc in Heptane

Procedimiento

To Diisopropylamine (22.001 mmol; 2240 mg; 3.13 mL) in THF (40 mL) at 0° C. was added N-Butyllithium (2.5 mol/L) in Hexane (24.001 mmol; 9.6 mL). The reaction was stirred at 0° C. for 0.5 h, and then cooled to −78° C. 2-bromo-6-fluoro-pyridine (20.001 mmol; 3520.0 mg) in THF (10 mL) was added dropwise. The mixture was stirred at −78° C. for 3 h. Iodomethane (22.001 mmol; 3122.8 mg; 1.37 mL) was added slowly. The mixture was allowed to warm to room temperature with stirring for 1 hour. The reaction was quenched with water (˜50 mL) and stirred overnight. The layers were separated. The organic layer was concentrated, and the residue was purified on silica eluted with 0 to 5% EtOAc in Heptane to afford 6-bromo-2-fluoro-3-methyl-pyridine as a white solid (2.08 g, 55%).

Fuente