反应详情

温度

60 °C

A mixture of 6-nitro-1H-indazole (50 g, 0.307 mol), 3-methoxypropyl methanesulfonate (54.3 g, 0.323 mol) and K2CO3 (127 g, 0.921 mol) in CH3CN (1.5 L) was heated at 60° C. overnight. Water (1 L) was added and the CH3CN was removed under reduced pressure and the aqueous residue was extracted with EtOAc (3×500 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel to give 1-(3-methoxypropyl)-6-nitro-1H-indazole (33 g, 46% yield). 1H NMR (400 MHz, CDCl3): δ8.47 (s, 1H), 8.13 (s, 1H), 8.01-7.99 (dd, J=8.8, 2.0 Hz, 1H), 7.83-7.81 (d, J=8.8 Hz, 1H), 4.61-4.57 (t, J=6.4 Hz, 2H), 3.29 (s, 3H), 3.26-3.23 (t, J=5.6 Hz, 2H), 2.23-2.17 (m, 2H).

1. customthe CH3CN was removed under reduced pressure
2. extractionthe aqueous residue was extracted with EtOAc (3×500 mL)
3. washThe combined organic extracts were washed with brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by column chromatography on silica gel