[F:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:10])[CH:5]=[C:6](F)[CH:7]=1.[C:16]1([SH:22])C=CC=CC=1.C[S-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH3:16][S:22][C:6]1[CH:5]=[C:4]([C:9]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:10])[CH:3]=[C:2]([F:1])[CH:7]=1To a solution of (3,5-difluorophenyl)(thiazol-2-yl)methanone from Thiophenol 2, Step 2, (1.09 g, 4.84 mmol) in DMF (4.8 mL) was added sodium thiomethoxide (0.34 g, 4.84 mmol). The mixture was stirred for 4 h at r.t., then added to sat. aqueous NH4Cl (100 mL) and extracted with EtOAc. The combined organic layers were washed with brine and dried over anhydrous MgSO4. Evaporation of the solvent and chromatography using hexane: EtOAc (90:10) gave 0.80 g of the title product.
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