反应详情

In a 25 mL round-bottomed flask, 1-(4-chloro-2-phenylamino-phenyl)-propan-1-one (522 mg, 2.01 mmol) was combined with THF (4 mL) to give a yellow solution. Sodium bis(trimethylsilyl)amide (1.0 M in THF) (5.02 mL, 5.02 mmol) was added slowly dropwise, resulting in a dark red solution. A mixture of oxazole-2-carbonyl chloride (344 mg, 2.61 mmol) in THF (8 mL) and 8 drops of DMF were added to the reaction mixture. The resulting mixture was stirred at room temperature for 5 hr. The reaction mixture was quenched by the addition of water and the aqueous layer was extracted with ethyl acetate. The organic phase was dried (MgSO4), filtered, then concentrated to afford a yellow oil. The crude material was purified by flash chromatography (silica gel, 80 g, 25-65% ethyl acetate in hexanes) to give 7-chloro-3-methyl-2-oxazol-2-yl-1-phenyl-1H-quinolin-4-one (160 mg, 23.6%) as a yellowish solid. MS calcd. for C19H13ClN2O2 [(M+H)+] 337, obsd. 337.

1. customto give a yellow solution
2. customresulting in a dark red solution
3. additionwere added to the reaction mixture
4. customThe reaction mixture was quenched by the addition of water
5. extractionthe aqueous layer was extracted with ethyl acetate
6. dry with materialThe organic phase was dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customto afford a yellow oil
10. customThe crude material was purified by flash chromatography (silica gel, 80 g, 25-65% ethyl acetate in hexanes)