تفاعل #42280

معادلة التفاعل

Ethylboronic acid

potassium carbonate

lithium chloride

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

→

title compound

Methyl 3-[(dipropylamino)carbonyl]-5-ethylbenzoate

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe mixture is then partitioned between ethyl acetate and water
2. 2
   أخرىThe phases are separated
3. 3
   غسيلthe ethyl acetate phase is washed with saline
4. 4
   تجفيفdried over sodium sulfate
5. 5
   تركيزconcentrated
6. 6
   أخرىchromatographed (silica gel; ethyl acetate/hexanes, 15/85)

الإجراء التجريبي

Ethylboronic acid (0.800 g, 10.8 mmol), dichlorobis(triphenylphosphine)-palladium(II) (0.252 g, 0.360 mmol), potassium carbonate (2.50 g, 18.0 mmol) and lithium chloride (0.151 g, 3.60 mmol) are added to a mixture of methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (1.23 g, 3.60 mmol) in dry DMF (20 mL). The mixture is heated at 100 degrees C. for 18 hours. The mixture is then partitioned between ethyl acetate and water. The phases are separated and the ethyl acetate phase is washed with saline, dried over sodium sulfate and concentrated. The concentrate is column chromatographed (silica gel; ethyl acetate/hexanes, 15/85) to give the title compound, MS (ESI+) for C17H25NO3 m/z (M+H)+=292.2.

المصدر