Sodium Carbonate → HCID 18446907, compound

Participants

Reaction Steps

Bromine (0.2 mL, 3.8 mmol) was added slowly to a solution of 4-(2-phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)pyridine (1.2 g, 3.41 mmol; Example 1, Step 2) in dry DCM at 0° C., followed by saturated aqueous Na2CO3 solution (40 mL). The reaction mixture was then stirred at rt for 16 h. The reaction was then allowed to partition and the layers separated. The aqueous phase was extracted with EtOAc (2×20 mL) and the combined organic phases were dried (Na2SO4). The resulting residue was purified by flash chromatography (SiO2, 100:0-90:10 DCM-MeOH) to furnish 1.06 g (72%) of 4-(5-bromo-2-phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)pyridine: 1H NMR (400 MHz, CDCl3) δ 8.62-8.70 (m, 2H), 7.78-8.05 (m, 2H), 7.77-7.86 (m, 2H), 7.45-7.54 (m, 3H), 5.37 (s, 2H), 3.60-3.70 (m, 2H), 0.92-1.02 (m, 2H), 0.003 (s, 9H).

Provenance & Evidence