反応 #72484

反応方程式

potassium tert-butoxide

1-naphthylamine

2,3-Dichloroquinoxaline

BINAP

→

Compound 2c

収率 33.0%

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

収率 33.0%

溶媒

反応条件

後処理

1. 1
   workup.ADDITIONadded to the reaction mixture which
2. 2
   温度was heated for 22 h
3. 3
   温度under reflux
4. 4
   温度After cooling to room-temperature
5. 5
   ろ過the reaction mixture was filtered
6. 6
   洗浄inorganic precipitate washed with dichloromethane (3×50 mL)
7. 7
   その他Removal of the solvent in vacuo
8. 8
   その他results in a residue which
9. 9
   その他was purified

実験手順

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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