反应详情

N-(4-Chlorobenzyl)-4-hydroxy-6-iodo-8-methoxy-3-quinolinecarboxamide (469 mg) from Example No. 117, copper (I) iodide (57 mg), and bis(triphenylphosphine)-palladium (II) chloride (35 mg) are suspended in diethylamine (15 mL). Propargyl alcohol (70 μL) is added and the mixture is allowed to stir at rt for 16 h. The reaction mixture is poured into water (50 mL) and extracted with ethyl acetate (2×50 mL). The organic layer is washed with saturated aqueous ammonium chloride (3×10 mL) and brine (10 mL). The aqueous layer is back-extracted with ethyl acetate (20 mL). The combined organic layers are dried (MgSO4) and concentrated. The crude product is purified by column chromatography (dichloromethane/methanol, 50/1; 33/1; 25/1; 20/1) to afford 289 mg (73%) of the title compound as a white solid.

1. extractionextracted with ethyl acetate (2×50 mL)
2. washThe organic layer is washed with saturated aqueous ammonium chloride (3×10 mL) and brine (10 mL)
3. extractionThe aqueous layer is back-extracted with ethyl acetate (20 mL)
4. dry with materialThe combined organic layers are dried (MgSO4)
5. concentrationconcentrated
6. customThe crude product is purified by column chromatography (dichloromethane/methanol, 50/1; 33/1; 25/1; 20/1)