[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[C:17]=2[F:24])=[S:14])=[O:11])[CH:7]=[C:6]([Cl:25])[N:5]=1.[CH3:26]I>C1COCC1>[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([NH:12][C:13](=[N:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[C:17]=2[F:24])[S:14][CH3:26])=[O:11])[CH:7]=[C:6]([Cl:25])[N:5]=1NaH (2.70 g, 0.06747 mol) was added carefully to a cooled solution (0° C.) of intermediate D9 (28.5 g, 0.04498 mol) in THF (200 ml). The mixture was stirred for 15 minutes and then CH3I (6.38 g, 0.04498 mol) was added. The ice-bath was removed and the reaction mixture was stirred for 2 hours at room temperature. Subsequently, the mixture was quenched with H2O and extracted with CH2Cl2 (3×100 ml). The combined organic layers were washed (brine), dried (MgSO4), filtered and the solvent was evaporated in vacuo. The residue was purified by flash chromatography (eluent: heptane/EtOAc gradiënt from 80/20 to 50/50). The desired fractions were collected and the solvent was evaporated. Yield: 5.7 g of intermediate D10 (32%).
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