Reaktion #42272

Reaktionsgleichung

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

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is cooled to 20-25 degrees C
2. 2
   Sonstigeand partitioned between water and ethyl acetate
3. 3
   SonstigeThe layers are separated
4. 4
   Waschenthe aqueous phase is back-washed with ethyl acetate
5. 5
   Waschenwashed three times with saline
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated

Vorschrift

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.

Quelle