[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([C:8]2[C:9]3[CH:16]=[CH:15][N:14]([S:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)(=[O:19])=[O:18])[C:10]=3[N:11]=[CH:12][N:13]=2)[CH:7]=1.C([N-]C(C)C)(C)C.[Li+].[I:36]I>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([C:8]2[C:9]3[CH:16]=[C:15]([I:36])[N:14]([S:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)(=[O:19])=[O:18])[C:10]=3[N:11]=[CH:12][N:13]=2)[CH:7]=1To a solution of Example 3B (2.5 g, 6.52 mmol) in 50 mL tetrahydrofuran at −78° C. was added 2M lithium diisopropylamide (4.89 mL, 9.78 mmol) over 5 minutes. The solution was stirred at −78° C. for 30 minutes and a solution of iodine (3.31 g, 13.04 mmol) in tetrahydrofuran (50 mL) was added over 5 minutes. The mixture was stirred at −78° C. for 2 hours and quenched with 50 mL 1M sodium thiosulfate. The aqueous layer was extracted with ethyl acetate (3×50 mL) and the combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound, which was used without further purification. MS (ESI+) m/z 509.51 (M+H)+.
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