反应详情

To a solution of 2-amino-3-nitropyridine (1.3 g, 9.3 mmol) in N,N-dimethylformamide (20 mL) was added 2-bromo-4′-fluoroacetophenone (2 g, 9.3 mmol) and the reaction mixture was heated at reflux for 6 hours. The resulting mixture was concentrated to a solid in vacuo. This residue was dissolved in dichloromethane and the organic phase was washed with aqueous sodium bicarbonate and an aqueous sodium chloride solution. The organic phase was dried (magnesium sulfate), filtered through a silica gel pad and concentrated to give a solid. This solid was recrystallized from methanol to give 870 mg (36%) of 2-(4-fluorophenyl)-8-nitroimidazo[1,2-α]pyridine as a brown solid. 1H NMR (d6-DMSO): δ 8.98 (d, 1H), 8.69 (s,1H), 8.32 (d, 1H), 8.10 (q, 2H), 7.36 (t, 2H), 7.15 (t, 1H); 19F NMR (DMSO-d6) δ −113.7; MS m/z 258 (M+1).

1. temperaturethe reaction mixture was heated
2. temperatureat reflux for 6 hours
3. concentrationThe resulting mixture was concentrated to a solid in vacuo
4. dissolutionThis residue was dissolved in dichloromethane
5. washthe organic phase was washed with aqueous sodium bicarbonate
6. dry with materialThe organic phase was dried (magnesium sulfate)
7. filtrationfiltered through a silica gel pad
8. concentrationconcentrated
9. customto give a solid
10. customThis solid was recrystallized from methanol