反应详情

Sodium hydride (60% dispersion in oil, 0.83 g, 21 mmol) was added to a solution of tert-butyl 4-(2-(6-bromopyridin-2-yl)hydrazono)azepane-1-carboxylate (6.4 g, 17 mmol) in DMF (54 mL) at room temperature under N2 and stirred for 20 min. Methyl iodide (1.1 mL, 18 mmol) was added to the solution, and the resulting solution was stirred for 2 h at ambient temperature. The mixture was quenched with H2O (100 mL). The solution was extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine (4×30 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford a dark orange oil. The oil was diluted with EtOAc (100 mL) and washed with brine (6×50 mL), dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to provide the title compound (7.00 g, quant.) as an amber oil: 1H NMR (300 MHz, DMSO-d6) δ 7.44-7.36 (m, 1H), 6.88 (d, J=7.2 Hz, 1H), 6.49-6.38 (m, 1H), 3.56-3.35 (m, 4H), 3.06-3.04 (m, 3H), 2.75-2.50 (m, 4H, overlaps with H2O), 1.72-1.51 (m, 2H), 1.43-1.15 (m, 9H).

1. stirringthe resulting solution was stirred for 2 h at ambient temperature
2. customThe mixture was quenched with H2O (100 mL)
3. extractionThe solution was extracted with EtOAc (2×50 mL)
4. washThe combined organic extracts were washed with brine (4×30 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto afford a dark orange oil
9. washwashed with brine (6×50 mL)
10. dry with materialdried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated to dryness under reduced pressure