Reacción #64636

Ecuación de reacción

4-tert-butylphenylethyne

4-tert-butylphenyl ethyne

Compound 19

4-tert-butylphenyl ethyne

ethyl-6-chloronicotinate

Compound 54

ethyl-6-chloronicotinate

→

title compound

Ethyl-6-(4-tert-butylphenylethynyl)nicotinate

Disolventes

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas degassed under nitrogen
2. 2
   TemperaturaThe mixture was then heated at 65 degrees C
3. 3
   workup.WAITfor 12 hours
4. 4
   Temperaturacooled to room temperature
5. 5
   Otrothe excess triethylamine removed under vacuum
6. 6
   Extracciónextracted with ether
7. 7
   OtroThe solvent was then removed in-vacuo
8. 8
   Otrothe residue purified by flash chromatography (silica 5% ethyl acetate in hexane)

Procedimiento

A mixture of 477.7 mg (3.02 mmol) of 4-tert-butylphenylethyne (Compound 19), 556.5 mg (3.01 mmol) of ethyl-6-chloronicotinate (Compound 54), 27.8 mg (0.15 mmol) of cuprous iodide, 58.7 mg (0.08 mmol) of bis(triphenylphosphine)palladium (II) chloride and 2 ml of triethylamine was degassed under nitrogen and then stirred under nitrogen at room temperature for 40 hours. The mixture was then heated at 65 degrees C. for 12 hours, cooled to room temperature and the excess triethylamine removed under vacuum. The residue was taken up in water and extracted with ether. The solvent was then removed in-vacuo and the residue purified by flash chromatography (silica 5% ethyl acetate in hexane) to give the title compound as a pale brown solid. PMR (CDCl3): & 1.33 (9H, s), 1.42 (3H, t, J~7.1 Hz); 4.42 (2H, q, J~7.1 Hz), 7.40 (2H, d, J~8.4 Hz), 7.53-7.61 (3H, m), 8.28 (1H, dd, J~8.1 Hz, 2.0 Hz), 9.20 (1H, d, J~2.0 Hz).

Fuente