[F:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[CH2:17][C@@H:16]3[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11][CH:10]=2)[N:6]=[CH:5]1.[I:23]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>ClCCl.FC(F)(F)C(O)=O>[F:1][CH2:2][CH2:3][N:4]1[C:8]([I:23])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[CH2:17][C@@H:16]3[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11][CH:10]=2)[N:6]=[CH:5]1To a solution of ethyl (1S,2S)-2-{4-[1-(2-fluoroethyl)-1H-imidazol-4-yl]phenyl}cyclopropanecarboxylate (450 mg, 1.488 mmol) in dichloromethane (5 mL) was added N-iodosuccinimide (352 mg, 1.563 mmol) and three drops trifluoroacetic acid. The reaction was stirred at rt for 3 h. The mixture was neutralized with aqueous sodium bicarbonate and the organics were extracted with dichloromethane. The organics were then washed with aqueous sodium thiosulfate, followed by three washes with water. The organics were dried (MgSO4), concentrated, and purified on 20 g of silica gel eluting a gradient of 35-100% ethyl acetate in hexanes to give rise to the title compound as a brown oil (110 mg, 0.257 mmol). LCMS: [M+1]+=429.
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