Reacción #42280

Ecuación de reacción

Ethylboronic acid

potassium carbonate

lithium chloride

methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate

→

title compound

Methyl 3-[(dipropylamino)carbonyl]-5-ethylbenzoate

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture is then partitioned between ethyl acetate and water
2. 2
   OtroThe phases are separated
3. 3
   Lavadothe ethyl acetate phase is washed with saline
4. 4
   Secadodried over sodium sulfate
5. 5
   Concentraciónconcentrated
6. 6
   Otrochromatographed (silica gel; ethyl acetate/hexanes, 15/85)

Procedimiento

Ethylboronic acid (0.800 g, 10.8 mmol), dichlorobis(triphenylphosphine)-palladium(II) (0.252 g, 0.360 mmol), potassium carbonate (2.50 g, 18.0 mmol) and lithium chloride (0.151 g, 3.60 mmol) are added to a mixture of methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (1.23 g, 3.60 mmol) in dry DMF (20 mL). The mixture is heated at 100 degrees C. for 18 hours. The mixture is then partitioned between ethyl acetate and water. The phases are separated and the ethyl acetate phase is washed with saline, dried over sodium sulfate and concentrated. The concentrate is column chromatographed (silica gel; ethyl acetate/hexanes, 15/85) to give the title compound, MS (ESI+) for C17H25NO3 m/z (M+H)+=292.2.

Fuente