反应详情

5-Bromo-2-ethoxy-3H-imidazole-4-carbaldehyde (10.0 g, 45.6 mmol), 4′-bromomethyl-3′-fluorobiphenyl-2-carboxylic acid t-butyl ester (16.7 g, 45.6 mmol) and potassium carbonate (9.5 g, 68.5 mmol) were dissolved in DMF (200 mL) at 0° C. After 10 minutes, the mixture was allowed to warm to room temperature and was stirred overnight. The mixture was filtered and concentrated in vacuo. The concentrate was extracted with EtOAc (2×200 mL) and sat. aq. NaHCO3:water; 1:1 (150 mL). The combined organic fractions were dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was recrystallized from EtOH (20 mL) and water (40 mL) to afford a white solid. The filtrate was concentrated in vacuo and purified by silica gel chromatography (EtOAc:hexanes) to yield the title compound as a white solid (3.6 g).

1. filtrationThe mixture was filtered
2. concentrationconcentrated in vacuo
3. extractionThe concentrate was extracted with EtOAc (2×200 mL) and sat. aq. NaHCO3
4. dry with materialThe combined organic fractions were dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude material was recrystallized from EtOH (20 mL) and water (40 mL)
8. customto afford a white solid
9. concentrationThe filtrate was concentrated in vacuo
10. custompurified by silica gel chromatography (EtOAc:hexanes)