CC#N.[Na+].[I-].C[Si](Cl)(C)C.[Br:11][C:12]1[C:13]2[CH:14]=[C:15]3[C:24]([CH2:26][C:27]([O:29][CH3:30])=[O:28])(O)[CH2:23][CH2:22][N:16]3[C:17]=2[CH:18]=[C:19]([F:21])[CH:20]=1.C([O-])(O)=O.[Na+]>CCOCC>[Br:11][C:12]1[C:13]2[CH:14]=[C:15]3[CH:24]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH2:23][CH2:22][N:16]3[C:17]=2[CH:18]=[C:19]([F:21])[CH:20]=1To dry CH3CN (2.3 g, 56 mmol) at r.t. was added NaI (8.4 g, 56 mmol) and trimethylsilyl chloride (6.1 g, 56 mmol). Then a solution of the alcohol of Step 7 (1.9 g, 5.6 mmol) in Et2O (60 mL) was slowly added. The reaction mixture was stirred for 5 minutes at r.t. and poured into a 1:1 mixture of saturated aqueous NaHCO3/10% aqueous Na2S2O3 (100 mL) at 0° C. The phases were separated and the aqueous layer was extracted with Et2O. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The desired compound was obtained as a brown solid (1.3 g).
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