Diiodomethane → 2-butyl-1-(2-hydroxy-2-methylpropyl)-5-iodo-1H-imidazole-4-carbonitrile

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To a solution of 5-amino-2-butyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazole-4-carbonitrile S4 (600 mg, 2.54 mmol, 1.0 equiv) and CH2I2 (2.0 mL) in CHCl3 (25 mL) at 80° C. was added a solution of isoamylnitrite (1.36 mL, 10.2 mmol, 4.0 equiv) in CHCl3 (5 mL) over 20 min. The reaction was stirred for additional 30 min at 80° C. then cooled to 25° C. The reaction was concentrated in vacuo and purification by silica gel column chromatography (1/9 EtOAc/hexanes-7/3 EtOAc/hexanes, gradient) afforded the title compound (687 mg, 78%) as a yellow solid: 1H NMR (CDCl3, 600 Hz) δ 0.88 (t, J=6.0 Hz, 3H), 1.29 (s, 6H), 1.33 (hex, J=7.8 Hz, 2H), 1.66 (pent, J=7.8 Hz, 2H), 2.88 (t, J=7.8 Hz, 2H), 3.95 (s, 2H); 13C NMR (CDCl3, 150 Hz) δ 13.7, 22.2, 28.3, 28.4, 29.6, 56.6, 71.6, 83.6, 115.1, 120.6, 155.4; MS (APCI+): calcd C12H19IN3O [M+H]+348.2. found 348.2.

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