4-Iodo-1-tritylimidazole → HCID 68705849, compound

Participants

Reaction Steps

To a solution of 4-iodo-1-trityl-1H-imidazole (Preparation described in Jetter, M. C., Boyd, R. E., Reitz, A. B. Org. Prep. Proced. Int. 1996, 28(6), 709-710; 87 mg, 0.20 mmol) in 2 mL TF was added ethylmagnesium bromide (1.0 M solution in THF, 0.24 mL, 0.24 mmol) dropwise. The reaction was stirred at rt for 0.5 h and zinc chloride (0.5 M solution in THF, 0.8 mL, 0.4 mmol) was added. After stirring for 1 h, 3-(5-((R)-2-tert-butoxycarbonylamino-1-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl)-5-bromo-N-methyl-N-(methylsulfonyl)benzenamine (100 mg, 0.18 mmol) and tetrakis(triphenylphosphine)palladium(0) (20.8 mg, 0.018 mmol) were added. The mixture was heated in a microwave oven to 80° C. for 0.5 h, quenched with saturated ammonium chloride and extracted with EtOAc. The combined organic layers were washed with water and brine. Drying, solvent evaporation and flash chromatography (15-65% EtOAc/hexanes) gave 3-(5-((R)-2-tert-butoxycarbonylamino-1-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl)-N-methyl-N-(methylsulfonyl)-5-(1-trityl-1H-imidazol-4-yl)benzenamine. 1H NMR (CDCl3) δ 8.23 (s, 1H), 7.98 (s, 1H), 7.87 (s, 1H), 7.54 (d, J=0.8 Hz, 1H), 7.40-7.00 (m, 21H), 3.56 (d, J=12 Hz, 1H), 3.44 (d, J=12 Hz, 1H), 3.39 (s, 3H), 2.92 (s, 3H), 1.72 (s, 3H), 1.41 (s, 9H).

Provenance & Evidence