[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19](/[CH:23]=[CH:24]/[O:25]C)[C:18]=3[O:27][CH3:28])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[I-].[Na+].C[Si](Cl)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][N:15]=[C:14]([C:17]3[C:18]([O:27][CH3:28])=[C:19]([CH2:23][CH:24]=[O:25])[CH:20]=[CH:21][CH:22]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]To a solution of 5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-3-{2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,2,4-thiadiazole (D102) (152 mg, 0.365 mmol) and sodium iodide (109 mg, 0.729 mmol) in Acetonitrile (10 mL) was added TMSCl (0.093 mL, 0.729 mmol) dropwise. The reaction mixture was stirred at room temperature overnight (16 h). The reaction was quenched with water (10 mL). Then EA (10 mL) was added to the reaction mixture. The organic phase was separated. The aqueous phase was extracted with EA (10 mL×2). The combined organic layers was dried over anhydrous sodium sulphate. After filtration and concentration, the residue was purified by column chromatography (EA/Hexane: 0 to 50%) to afford [3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-(methyloxy)phenyl]acetaldehyde (D103) (87.6 mg). MS (ES): C20H19ClN2O3S requires 402.1. found 403.1 (M+H+).
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