Réaction #42280

Équation de réaction

Ethylboronic acid

potassium carbonate

lithium chloride

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

→

title compound

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

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreThe mixture is then partitioned between ethyl acetate and water
2. 2
   AutreThe phases are separated
3. 3
   Lavagethe ethyl acetate phase is washed with saline
4. 4
   Séchagedried over sodium sulfate
5. 5
   Concentrationconcentrated
6. 6
   Autrechromatographed (silica gel; ethyl acetate/hexanes, 15/85)

Mode opératoire

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.

Source