Réaction #155321

Équation de réaction

dimethoxyethane

3-Iodo-5-propoxy-4H-benzo[f]quinolin-1-one

water

sodium carbonate

→

2-furan-3-yl-5-propoxy-4H-benzo[f]quinolin-1-one

Rendement 48.0%

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was cooled to room temperature
2. 2
   Extractionthe resulting mixture was subjected to extraction
3. 3
   ConcentrationThe thus-obtained organic layer was concentrated under reduced pressure
4. 4
   Autrethe residue was purified
5. 5
   ConcentrationThe purified product was concentrated under reduced pressure
6. 6
   Lavagethe residue was washed with ethyl acetate
7. 7
   Autredried

Mode opératoire

3-Iodo-5-propoxy-4H-benzo[f]quinolin-1-one (1.06 g, 2.79 mmol) was suspended in dimethoxyethane (20 ml). Furan-3-boron acid (354 mg, 3.16 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II)-dichloromethane complex (PdCl2(DPPF).CH2Cl2, 123 mg, 0.11 mmol) and a 2N aqueous sodium carbonate solution (4.0 ml) were sequentially added to the suspension. The mixture was stirred at 90 to 100° C. under a nitrogen atmosphere for hours. The reaction mixture was cooled to room temperature, water was added thereto, and the resulting mixture was subjected to extraction using dichloromethane. The thus-obtained organic layer was concentrated under reduced pressure, and the residue was purified using silica gel column chromatography (dichloromethane:ethyl acetate=80:1). The purified product was concentrated under reduced pressure, the residue was washed with ethyl acetate and then dried, giving a pale brown powder of 2-furan-3-yl-5-propoxy-4H-benzo[f]quinolin-1-one (430 mg, yield: 48%).

Source