反应详情

温度

-78 °C

A solution of lithium diisopropylamide (5.52 g) in anhydrous THF (80 ml) was added dropwise over 1 h to a stirred solution of the product of step c) (8.02 g) and 4-quinolinecarboxaldehyde (8.12 g) in anhydrous THF (80 ml) at −78° C. under nitrogen. The mixture was stirred for a further 1 hour at −78° C. then quenched with glacial acetic acid (10 ml), allowed to warm to room temperature, diluted with saturated sodium bicarbonate solution (100 ml) and extracted into ethyl acetate (2×100 ml). The combined extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography, eluting with 3:2 ethyl acetate/i-hexane, to give the sub-title compound as a white solid (7.35 g). MS(ESI) 468 {M+H]+. δ 1HCDCl3 0.85 (3H,d), 0.88 (3H,d), 1.43 (3H,t), 2.10-2.16 (1H,m), 3.38 (3H,s), 3.49 (1H,dd), 3.61 (1H, s,br), 3.71 (1H,dd), 4.48 (2H,quartet), 6.78 (1H,s), 7.52 (1H,t), 7.72 (1H,t), 7.83 (1H,d), 7.90 (1H,d), 8.17 (1H,d), 9.02 (1H,d)

1. customthen quenched with glacial acetic acid (10 ml)
2. temperatureto warm to room temperature
3. additiondiluted with saturated sodium bicarbonate solution (100 ml)
4. extractionextracted into ethyl acetate (2×100 ml)
5. dry with materialThe combined extracts were dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by column chromatography
9. washeluting with 3:2 ethyl acetate/i-hexane