反応 #42280

反応方程式

Ethylboronic acid

potassium carbonate

lithium chloride

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

→

title compound

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

溶媒

DMF

反応条件

後処理

1. 1
   その他The mixture is then partitioned between ethyl acetate and water
2. 2
   その他The phases are separated
3. 3
   洗浄the ethyl acetate phase is washed with saline
4. 4
   乾燥dried over sodium sulfate
5. 5
   濃縮concentrated
6. 6
   その他chromatographed (silica gel; ethyl acetate/hexanes, 15/85)

実験手順

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.

出典