Methyl iodide → 2-Bromo-6-ethylpyridine

Temperature

-78 °C

To a solution of 2-bromo-6-methylpyridine (302 mg, 1.76 mmol) an 10 mL THF at −78° C., was added a solution of lithium diisopropylamide (1.8 M in heptane/THF/ethylbenzene, 1.07 mL, 1.93 mmol). The bright orange/red mixture was treated with iodomethane (0.20 mL, 3.2 mmol). The mixture was stirred at −78° C. for 10 min, then was removed from the ice bath and stirred 30 min. The reaction was quenched with sat. NH4Cl, then was diluted with EtOAc. The organic phase was washed with water (2×) and brine, dried (Na2SO4) and concentrated. The crude residue was purified by flash chromatography (0 to 20% EtOAc/hexanes gradient) to afford 157 mg of Intermediate 163.1 as a colorless oil. LCMS (2 min gradient) RT=1.26 min, 186.0 (M+H)+.

1. customwas removed from the ice bath
2. stirringstirred 30 min
3. customThe reaction was quenched with sat. NH4Cl
4. additionwas diluted with EtOAc
5. washThe organic phase was washed with water (2×) and brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated
8. customThe crude residue was purified by flash chromatography (0 to 20% EtOAc/hexanes gradient)

ORD record

ord-4a8ca097df2f422fa362a24104afb9eb

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576098B2