反应详情

A suspension of sodium hydride (95%, 0.96 g, 40 mmol) in dimethylacetamide (60 mL) at 10° C. under nitrogen was reacted with the product of Example 1A (5.7 g, 34.7 mmol) with stirring for 1 hour then treated with n-butylbromide (5.2 g, 38 mmol) and stirred for an additional 16 hours. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated under vacuum. The crude product was purified by flash column chromatography with silica gel eluting with hexane and ethyl acetate (3:1) to give the title compound as a white solid, (2.5 g, 33% yield). 1H NMR (300 MHz, DMSO-d6) δ 0.92 (t, J=7.35 Hz, 3H), 1.36 (m, 2H), 1.65 (m, 2H), 4.13 (m, 2H), 7.38 (dd, J=7.72, 4.78 Hz, 1H), 8.39 (dd, J=7.72, 1.84 Hz, 1H), 8.77 (dd, J=5.15, 1.84 Hz, 1H).

1. stirringstirred for an additional 16 hours
2. customThe reaction was partitioned between ethyl acetate and water
3. washThe organic layer was washed with water and brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under vacuum
7. customThe crude product was purified by flash column chromatography with silica gel eluting with hexane and ethyl acetate (3:1)