反应详情

To a solution of 0.913 g (5.2 mmol) of 7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine in 10 mL of anhydrous dimethylformamide was added 0.210 g (5.7 mmol) of a 60% mineral oil dispersion of sodium hydride. The reaction mixture was magnetically stirred under a nitrogen atmosphere for 2 hours, at which point 1.675 g (5.7 mmol) of 4-bromomethyl-2'-nitrobiphenyl was added as a solid. The reaction mixture was stirred an additional 1 hour at room temperature, then partitioned between ethyl acetate and water. The organic layer was extracted, washed with brine, dried (MgSO4), filtered and evaporated. The residual oil was purified on a silica gel flash chromatography column eluted with 75% ethyl acetate-hexane, which after evaporation of the pure fractions and drying in vacuo afforded 1.009 g (50%) of the product as a tan solid: NMR (CDCl3) δ 0.97 (t, J=8 Hz, 3H), 1.70-1.83 (m, 2H), 2.66 (s, 3H), 2.81 (t, J=10 Hz, 2H), 5.52 (s, 2H), 7.02 (d, J=6 Hz, 1H), 7.14-7.25 (m, 4H), 7.36 (d, J=10 Hz, 1H), 7.42-7.48 (m, 1H), 7.56-7.61 (m, 1H), 7.82 (d, J=10 Hz, 1H), 8.20 (d, J=6 Hz, 1H); MS (FAB) m/e 387 (MH+).

1. additionwas added as a solid
2. custompartitioned between ethyl acetate and water
3. extractionThe organic layer was extracted
4. washwashed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customevaporated
8. customThe residual oil was purified on a silica gel flash chromatography column
9. washeluted with 75% ethyl acetate-hexane, which
10. customafter evaporation of the pure fractions
11. customdrying in vacuo