반응 #42280

반응 방정식

Ethylboronic acid

potassium carbonate

lithium chloride

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

→

title compound

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

용매

DMF

반응 조건

후처리

1. 1
   기타The mixture is then partitioned between ethyl acetate and water
2. 2
   기타The phases are separated
3. 3
   세척the ethyl acetate phase is washed with saline
4. 4
   건조dried over sodium sulfate
5. 5
   농축concentrated
6. 6
   기타chromatographed (silica gel; ethyl acetate/hexanes, 15/85)

실험 절차

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.

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