[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:3]=12.C([N-]C(C)C)(C)C.[Li+].[I:28]I>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:9]([I:28])=[CH:10][C:3]=12To a −78° C. solution of Example 135A (250 mg, 0.741 mmol) in 10 mL tetrahydrofuran was added lithium diisopropylamide (2.0M solution in tetrahydrofuran, 0.556 mL, 1.112 mmol) slowly over the course of 5 minutes. The resulting solution was stirred at the same temperature for 30 minutes after which iodine (376 mg, 1.483 mmol) in 5 mL of tetrahydrofuran was slowly added over 10 minutes. The reaction was stirred at −78° C. for 2.5 hours, and was quenched by addition of 1M aqueous sodium thiosulfate solution. The mixture was extracted with dichloromethane. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated to give the title compound. MS (ESI+) m/z 462 (M+1).
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