تفاعل #42272

معادلة التفاعل

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

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture is cooled to 20-25 degrees C
2. 2
   أخرىand partitioned between water and ethyl acetate
3. 3
   أخرىThe layers are separated
4. 4
   غسيلthe aqueous phase is back-washed with ethyl acetate
5. 5
   غسيلwashed three times with saline
6. 6
   تجفيفdried over anhydrous magnesium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated

الإجراء التجريبي

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.

المصدر