Triethylamine → 1-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-(1-(trimethylsilyloxy)ethenyl)-1H-imidazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 2.50 g (6.81 mmol) of 1-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-acetyl-1H-imidazole (67 R1 =2-F, R2 =4-Br, n=0; prepared using the procedures of Example 3, Parts A and B) in 80 mL anhydrous THF was added 7.59 mL trimethylsilyl triflate (40.8 mmol) under nitrogen at 22° C., followed by 11.38 mL (81.9 mmol) triethylamine. The mixture was stirred at 22° C. for 2.5 hours and then diluted with 100 mL of anhydrous ethyl ether and quenched with 10 mL of saturated NaHCO3 solution. The organic layer was washed with saturated NaHCO3 solution, dried over Na2SO4, and filtered. Solvents were then removed under reduced pressure yield 2.69 g (90%) of the title compound as a brown oil, which was used without further purification. 1H NMR (300 MHz, CDCl3): δ 0.14 (s, 9H); 0.84 (t, 3H); 1.16 (t, 3H); 1.68 (m, 2H); 2.41 (t, 2H); 2.56 (q, 2H); 4.30 (s, 1H); 4.43 (s, 1H); 5.03 (s, 2H); 6.44 (t, 1H); 7.10 (m, 2H). ##STR103##

Provenance & Evidence