Reacción #42272

Ecuación de reacción

1,3-bis(diphenylphosphino)propane

hexamethyldisilazane

diisopropylethylamine

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

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

N-methyl pyrrolidinone

→

title compound

Methyl 3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]-benzoate

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is cooled to 20-25 degrees C
2. 2
   Otroand partitioned between water and ethyl acetate
3. 3
   OtroThe layers are separated
4. 4
   Lavadothe aqueous phase is back-washed with ethyl acetate
5. 5
   Lavadowashed three times with saline
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated

Procedimiento

To a mixture of methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (XXI, PREPARATION 3, 0.5 g, 1.47 mmol) in dry N-methyl pyrrolidinone under a carbon monoxide atmosphere is added palladium (II) acetate (0.017 g, 0.074 mmol), 1,3-bis(diphenylphosphino)propane (0.045 g, 0.11 mmol), hexamethyldisilazane (1.0 mL, 4.7 mmol), and diisopropylethylamine (0.38 g, 2.94 mmol). The mixture is heated at 100 degrees C. for 24 hours. The mixture is cooled to 20-25 degrees C. and partitioned between water and ethyl acetate. The layers are separated and the aqueous phase is back-washed with ethyl acetate. The organic phases are combined and washed three times with saline, dried over anhydrous magnesium sulfate, filtered and concentrated. Column chromatography (silica gel, 75 mL; methanol/methylene chloride, 2.5/97.5) gives the title compound, NMR (CDCl3) delta 0.77, 1.02, 1.57, 1.71, 3.17, 3.49, 3.98, 5.78, 6.34, 8.07, 8.20 and 8.48.

Fuente