Reaktion #590812

Reaktionsgleichung

1-Chloro-2-(methylsulfonyl)ethane

NaI

4-(4-(4-(4-chlorophenyl)phthalazin-1-ylamino)phenylthio)quinolin-6-ol

NaH

→

4-(4-chlorophenyl)-N-(4-(6-(2-(methylsulfonyl)ethoxy)quinolin-4-ylthio)phenyl)phthalazin-1-amine

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred
2. 2
   Temperaturwarmed to RT for 15 h
3. 3
   SonstigeThe reaction was quenched with sat. NH4Cl
4. 4
   Extraktionextracted with DCM
5. 5
   WaschenThe combined organic layers were washed with brine
6. 6
   Sonstigedried
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe crude product was purified via column chromatography on silica gel (
10. 10
    WaschenRediSep 40 g column, gradient elution with 0-50% (90:10:1 DCM/MeOH/NH4OH-DCM)

Vorschrift

To a solution of 4-(4-(4-(4-chlorophenyl)phthalazin-1-ylamino)phenylthio)quinolin-6-ol (0.062 g, 0.12 mmol) in THF at 0° C., was added NaH (0.018 g, 0.73 mmol). The mixture was stirred at 0° C. for 30 minutes. 1-Chloro-2-(methylsulfonyl)ethane (0.035 g, 0.24 mmol) and trace amount of NaI were added. The mixture was stirred and warmed to RT for 15 h. The reaction was quenched with sat. NH4Cl, and extracted with DCM. The combined organic layers were washed with brine, dried, filtered and concentrated. The crude product was purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-50% (90:10:1 DCM/MeOH/NH4OH-DCM) to afford 4-(4-chlorophenyl)-N-(4-(6-(2-(methylsulfonyl)ethoxy)quinolin-4-ylthio)phenyl)phthalazin-1-amine as a light yellow solid. MS: m/z=[M+H]+. 614.0 Calc'd for C32H25ClN4O3S2: 613.1.

Quelle