반응 #42272

반응 방정식

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

반응 조건

후처리

1. 1
   온도The mixture is cooled to 20-25 degrees C
2. 2
   기타and partitioned between water and ethyl acetate
3. 3
   기타The layers are separated
4. 4
   세척the aqueous phase is back-washed with ethyl acetate
5. 5
   세척washed three times with saline
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated

실험 절차

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.

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