反应详情

1.05 g (5 mmol) of β-carboline-3-carbaldehyde oxime is suspended in 50 ml of dry THF and combined at 0° C. with 1.8 g of N-bromosuccinimide in 20 ml of dry THF. The reaction mixture is heated to room temperature, stirred for 95 hours, and combined with 1.5 eq. of trimethylsilylacetylene and 2 ml of triethylamine. The mixture is further stirred overnight, poured on ice water, and extracted with ether. The organic phase is dried over magnesium sulfate, filtered, and the solvent drawn off. The remaining oil is dissolved in 10 ml of DMF and combined with 10 ml of sodium hydroxide solution (1-molar). The reaction mixture is stirred overnight at room temperature, poured on water, and extracted with ethyl acetate. The resultant product is purified by column chromatography with ethyl acetate as the eluent. Melting point: 292°-293° C.

1. waitThe mixture is further stirred overnight
2. additionpoured on ice water
3. extractionextracted with ether
4. dry with materialThe organic phase is dried over magnesium sulfate
5. filtrationfiltered
6. dissolutionThe remaining oil is dissolved in 10 ml of DMF
7. stirringThe reaction mixture is stirred overnight at room temperature
8. additionpoured on water
9. extractionextracted with ethyl acetate
10. customThe resultant product is purified by column chromatography with ethyl acetate as the eluent