Reaktion #72484

Reaktionsgleichung

potassium tert-butoxide

1-naphthylamine

2,3-Dichloroquinoxaline

BINAP

→

Compound 2c

Ausbeute 33.0%

(3-Chloro-quinoxalin-2-yl)-naphthalen-1-yl-amine

Ausbeute 33.0%

Lösungsmittel

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONadded to the reaction mixture which
2. 2
   Temperaturwas heated for 22 h
3. 3
   Temperaturunder reflux
4. 4
   TemperaturAfter cooling to room-temperature
5. 5
   Filtrationthe reaction mixture was filtered
6. 6
   Wascheninorganic precipitate washed with dichloromethane (3×50 mL)
7. 7
   SonstigeRemoval of the solvent in vacuo
8. 8
   Sonstigeresults in a residue which
9. 9
   Sonstigewas purified

Vorschrift

BINAP (93.3 mg, 0.15 mmol) and palladium acetate (22.6 mg, 0.1 mmol) were dissolved in dry xylenes (50 mL) and stirred for 10 min in an inert atmosphere of nitrogen. 2,3-Dichloroquinoxaline (1.99 g, 10 mmol), 1-naphthylamine (1.50 g, 10.5 mmol) and potassium tert-butoxide (1.34 g, 12 mmol) were the added to the reaction mixture which was heated for 22 h under reflux. After cooling to room-temperature, the reaction mixture was filtered and inorganic precipitate washed with dichloromethane (3×50 mL). Removal of the solvent in vacuo results in a residue which was purified using silica gel chromatography (hexanes/EtOAc 9:1). Compound 2c was isolated as yellow-orange crystals, mp=157-159° C. Yield 33%. TLC Rf=0.45 (hexanes/EtOAc 3:1). HPLC/MS: [M+H]+ m/z 306. 1H NMR (CDCl3, 600 MHz): δ 7.50 (td, J=7.2 Hz, 1.2 Hz, 1H), 7.56-7.63 (m, 4H), 7.74 (d, J=8.4 Hz, 1H), 7.78 (dd, J=8.4 Hz, 1.2 Hz, 1H), 7.89 (dd, J=8.4 Hz, 1.2 Hz, 1H), 7.90 (d, J=8.4 Hz, 1H), 7.99-8.04 (m, 2H), 8.54 (d, J=7.2 Hz, 1H). 13C NMR (CDCl3, 150 MHz): δ 118.62, 120.31, 125.01, 125.85, 126.10, 126.26, 126.45, 126.74, 126.79, 127.89, 129.01, 130.42, 133.25, 134.26, 137.25, 138.12, 140.59, 145.71. HRMS: Calcd. for C18H13ClN3 [M+H]+ m/z 306.0793, Observed 306.0786.

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