Reacción #1605846

Ecuación de reacción

chloromethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate

cesium acetate

→

acetoxymethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate

Disolventes

ethyl acetate

dimethyl formamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched with water/brine (1:1, 50 mL)
2. 2
   ExtracciónThe reaction was extracted with ethyl acetate (3×50 mL)
3. 3
   LavadoThe combined organics were washed with water (50 mL)
4. 4
   Secadobrine (50 mL) and dried (MgSO4)
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe crude product was purified by column chromatography on silica eluting with 0-10% tetrahydrofuran/dichloromethane with 1% Et3N
7. 7
   Otroto give the product which
8. 8
   Otropurification
9. 9
   OtroThe product was purified by column chromatography on silica eluting with 0.5% Et3N/ethyl acetate

Procedimiento

To a solution of chloromethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (1.20 g, 2.22 mmol) in dimethyl formamide (20 mL) was added cesium acetate (639 mg, 3.33 mmol). The reaction was then stirred at ambient temperature overnight. The reaction was diluted with ethyl acetate (50 mL) and quenched with water/brine (1:1, 50 mL). The reaction was extracted with ethyl acetate (3×50 mL). The combined organics were washed with water (50 mL) then brine (50 mL) and dried (MgSO4) and concentrated. The crude product was purified by column chromatography on silica eluting with 0-10% tetrahydrofuran/dichloromethane with 1% Et3N to give the product which required further purification. The product was purified by column chromatography on silica eluting with 0.5% Et3N/ethyl acetate to give acetoxymethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate, Compound-87 (243 mg, 19% over 2 steps).

Fuente