Reaction Steps
1-(2-fluoro-4-iodobenzyl)-4-ethyl-2-propyl-1H-imidazole-5-phenoxyphenethyl ketone (2.35 g, 3.90 mmol), 2-(t-butylamino)sulfonylphenyl boronic acid (1.52 g, 5.85 mmol), and soduim carbonate (10 mL of 2M aqueous solution), and tetrabutylammonium bromide (65 mg, o.20 mmol) were added together with 50 mL of toluene. Tetrakis(triphenylphosphine) palladium(O) (0.23 g, 0.20 mmol) was added. The mixture was refluxed under N2 overnight. The solvent was removed in vacuo and the residue was partitioned between H2O and CH2Cl2. The aqueous layer was extracted with CH2Cl2, and the combined organic solution was washed with brine, dried over MgSO4 and concentrated. The crude product was purified by flash column chromatography (silica gel, 30% EtOAc/hexane) to give 1.92 g of light yellow foam (72%). MS m/e 682.5, [M+H]+ ; 1H NMR (300 MHz, CDCl3): δ 0.96 (t, 3H, CH3), 0.98 (t, 9H, CH3), 1.27 (t, 3H, CH3), 1.69 (m, 2H, CH2), 2.60 (t, 2H, CH2), 2.85 (q, 2H, CH2), 2.97 (m, 2H, CH2), 3.13 (m, 2H, CH2), 3.58 (s, 1H, NH), 5.57 (s, 2H, CH2Ar), 6.60 (t, 1H, ArH), 6.86 (d, 1H, ArH), 6.92 (d, 2H, ArH), 7.05 (d, 2H, ArH), 7.16 (m, 2H, ArH), 7.26 (m,5H, ArH), 7.55 (m, 2H, ArH), 8.16 (m, 1H, ArH). ##STR67##
