Реакция #42280

Уравнение реакции

Ethylboronic acid

potassium carbonate

lithium chloride

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

→

title compound

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

Растворители

DMF

Условия реакции

Обработка

1. 1
   ДругоеThe mixture is then partitioned between ethyl acetate and water
2. 2
   ДругоеThe phases are separated
3. 3
   Промывкаthe ethyl acetate phase is washed with saline
4. 4
   Сушкаdried over sodium sulfate
5. 5
   Концентрированиеconcentrated
6. 6
   Другоеchromatographed (silica gel; ethyl acetate/hexanes, 15/85)

Методика

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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