FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C(N(C(C)C)CC)(C)C.[CH2:25]([N:27]([CH2:38][CH3:39])[C:28](=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35]O)[CH3:26].C(OC([N:47]1[CH:51]=[C:50]([I:52])[N:49]=[CH:48]1)=O)(C)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:25]([N:27]([CH2:38][CH3:39])[C:28](=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][N:49]1[C:50]([I:52])=[CH:51][N:47]=[CH:48]1)[CH3:26]A flask is charged with dichloromethane (200 mL) and trifluoromethanesulfonic anhydride (19.34 g, 67.20 mmol) and cooled to −78° C. A solution of diisopropylethylamine (9.57 g, 73.30 mmol) and N,N-diethyl-2-hydroxymethyl-benzamide (12.92 g, 61.09 mmol) in dichloromethane (40 mL) is added over 10 min. After 30 min, a solution of 4-iodo-imidazole-1-carboxylic acid tert-butyl ester (12.83 g, 42.76 mmol) in dichloromethane (40 mL) is added. The mixture is allowed to gradually warm overnight and after 18 h, saturated aqueous sodium bicarbonate (100 mL) is added and the mixture is stirred vigorously for 30 min. The aqueous layer is extracted with dichloromethane. The combined organic phase is dried over MgSO4, filtered through a cotton plug and concentrated in vacuo. The residue is purified by silica gel flash chromatography (dichloromethane-methanol, 49:1) to afford N,N-diethyl-2-(5-iodo-imidazol-1-ylmethyl)-benzamide; MS (ESI) m/z 384.1 (M+H).
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