Reaktion #168148

Reaktionsgleichung

Na2CO3

(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-[(S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl]-1,3-oxazinan-2-one

6-chloro-2,4-dimethyl-2H-pyridazin-3-one

→

title compound

3-{(S)-1-[4-(1,5-Dimethyl-6-oxo-1,6-dihydro-pyridazin-3-yl)-phenyl]-ethyl}-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting mixture was sparged with argon for 10 min, before [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II)dichloromethane complex (15 mg)
2. 2
   workup.ADDITIONwas added
3. 3
   TemperaturAfter cooling to ambient temperature
4. 4
   workup.ADDITIONwater was added
5. 5
   Extraktionthe resulting mixture was extracted with ethyl acetate
6. 6
   WaschenThe combined organic extracts were washed with brine
7. 7
   Trocknendried (MgSO4)
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe residue was purified by chromatography on silica gel (CH2Cl2/MeOH 98:2→80:20)

Vorschrift

2 M aqueous Na2CO3 solution (0.31 mL) was added to a solution of (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-[(S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl]-1,3-oxazinan-2-one (0.15 g) and 6-chloro-2,4-dimethyl-2H-pyridazin-3-one (75 mg) in N,N-dimethylformamide (1 mL). The resulting mixture was sparged with argon for 10 min, before [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II)dichloromethane complex (15 mg) was added. The mixture was heated to 100° C. and stirred at this temperature overnight. After cooling to ambient temperature, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated. The residue was purified by chromatography on silica gel (CH2Cl2/MeOH 98:2→80:20) to afford the title compound.

Quelle