反応 #42272

反応方程式

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

反応条件

後処理

1. 1
   温度The mixture is cooled to 20-25 degrees C
2. 2
   その他and partitioned between water and ethyl acetate
3. 3
   その他The layers are separated
4. 4
   洗浄the aqueous phase is back-washed with ethyl acetate
5. 5
   洗浄washed three times with saline
6. 6
   乾燥dried over anhydrous magnesium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated

実験手順

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.

出典