Reaktion #90190

Reaktionsgleichung

7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

7-Methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

Compound A2

7-Methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

3-bromo-4-chloro-pyridine

sodium t-butoxide

S-Phos

→

title compound

Ausbeute 4.0%

8-Methoxy-10,10-dimethyl-5,10-dihydro-11-oxa-3-aza-benzo[b]fluorene

Ausbeute 4.0%

Lösungsmittel

ethyl acetate

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Filtrationfiltered through Celite
3. 3
   WaschenThe organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine
4. 4
   TrocknenThereafter, the organic layer was dried over sodium sulfate
5. 5
   SonstigeThe residues obtained
6. 6
   Einengenafter concentration under reduced pressure
7. 7
   Sonstigewere purified by silica gel column (ethyl acetate/hexane)

Vorschrift

To 7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound A2, 2.5 g), 3-bromo-4-chloro-pyridine (2 g), sodium t-butoxide (3 g), Pd2dba3 (476 mg), and S-Phos (512 mg), toluene (20 ml) was added, and the mixture was stirred and heated at 100° C. overnight under nitrogen atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate and filtered through Celite. The organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine. Thereafter, the organic layer was dried over sodium sulfate. The residues obtained after concentration under reduced pressure were purified by silica gel column (ethyl acetate/hexane) to obtain the title compound (112 mg, 4%).

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