反应详情

To a solution of 4-benzenesulfinyl-6,7-dimethoxy-quinoline (step b, 1 g, 3.2 mmol) in THF (15 mL) at −10° C., was added phenylmagnesium bromide (1M in THF, 3.5 mL, 3.5 mmol). The reaction was warmed to RT and stirred for 20 min. 6-Bromo-naphthalene-2-carbaldehyde (Step d, 0.75 g, 3.2 mmol) was added in THF. The resulting mixture was stirred at RT for 2 h, then poured into saturated NH4Cl solution and extracted with ethyl acetate 3×. The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by silica gel column chromatography (15-35% acetone/CH2Cl2) to give the titled compound. MS (ESI, pos. ion) m/z: 424.1 (M+1).

1. stirringThe resulting mixture was stirred at RT for 2 h
2. extractionextracted with ethyl acetate 3×
3. washThe combined organic layer was washed with brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude was purified by silica gel column chromatography (15-35% acetone/CH2Cl2)