Reacción #52309

Ecuación de reacción

3-bromo-5-methanesulfonyl-pyridine

3,3,3-triethoxypropyne

triethylamine

→

title compound

Rendimiento 87.3%

3-Methanesulfonyl-5-triethoxyprop-1-ynyl-pyridine

Rendimiento 87.3%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 48 h
2. 2
   Otrothe solvent was removed under reduced pressure
3. 3
   OtroThe crude product was chromatographed on silica (30% ethyl acetate/hexanes)

Procedimiento

A solution of 3-bromo-5-methanesulfonyl-pyridine (1.00 g, 4.20 mmol), 3,3,3-triethoxypropyne (1.75 g, 9.4 mmol), dichlorobis(triphenylphospine)palladium(II) (0.15 g, 0.21 mmol), copper(I)iodide (0.08 g, 0.42 mmol), triethylamine (1.80 mL, 12.7 mmol) and dichloromethane (40 mL) was heated at reflux for 48 h. The mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude product was chromatographed on silica (30% ethyl acetate/hexanes) to give the title compound (1.2 g, 87% yield) as yellow solid. 1H NMR (CDCl3) δ 9.08(d, 1H, J=2.4 Hz), 8.91 (d, 1H J=2.0), 8.28 (t, 1H, J=2.0 Hz), 3.75 (q, 6H, J=7.2), 3.13 (s, 3H), 1.29 (t, 9H, J=7.2).

Fuente