반응 #140

반응 방정식

O=c1cc(N2CCOCC2)oc2c

CCN1CCNCC1

→

CCN1CCN(c2ccc(-c3ccc

수율 48.7%

용매

Cc1ccccc1

반응 조건

실험 절차

8-(1-iododibenzo[b,d]thiophen-4-yl)-2-morpholino-4H-chromen-4-one (2 g, 3.71 mmol), 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (0.462 g, 0.74 mmol), CESIUM CARBONATE (3.62 g, 11.12 mmol) and PALLADIUM (II) ACETATE (0.166 g, 0.74 mmol) were weighed out in a flask and inerted with argon. toluene (25 ml) and 1-ethylpiperazine (0.942 ml, 7.42 mmol) were added and the mixture was degassed several times with argon. The reaction was stirred at 110 °C (bath) for 2 hours. The reaction was incomplete. 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (0.462 g, 0.74 mmol) and PALLADIUM (II) ACETATE (0.166 g, 0.74 mmol) were added, the reaction mixture was purged with argon, and the mixture was stirred at 110 °C for 5 hours. Reaction was quite clean: Crude LCMS showed very little de-iodo by-product and starting material left. The reaction was diluted with dichloromethane and insolubles were removed by filtration. The filtrate was concentrated to dryness. The crude product was purified by flash chromatography on silica gel eluting with 0 to 5% methanol in dichloromethane. The solvent was evaporated, the resulting solid was stirred in diethyl ether (40 ml) for 2 days. The product was filtered to give a solid which was collected by filtration and dried under vacuum to give 8-(1-(4-ethylpiperazin-1-yl)dibenzo[b,d]thiophen-4-yl)-2-morpholino-4H-chromen-4-one (0.950 g, 48.7 %) as a pale beige solid. Melting point: 221-224°C Purity check: 99%, Et2O: 0.06 mole/mole, H2O: 0.3 mole/mole H NMR strength: 97% +/- 3%

출처