C[O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1.[Na+].[I-].[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][C:22]=1[F:29]>C(#N)C>[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:8]2[CH:7]=[C:6]([C:9]3[S:10][C:11]4[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=4[N:13]=3)[CH:5]=[CH:4][C:3]2=[O:2])=[CH:23][C:22]=1[F:29]According to Scheme 4, Step 1: A mixture of 2-(6-methoxypyridin-3-yl)benzo[d]thiazole (1 eq, 0.25 mmol, 60 mg), NaI (5 eq, 1.20 mmol, 0.19 g) and 4-chloro-3-fluorobenzylbromide (5 eq, 1.20 mmol, 0.28 g) in acetonitrile (10 mL) was stirred for 14 hours at 90° C. The crude residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered and evaporated. The crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/AcOEt 95/5 as eluent to afford 1-(4-chloro-3-fluorobenzyl)-5-(benzo[d]thiazol-2-yl)pyridin-2(1H)-one (0.14 mmol, 0.05 g, 58%) as a beige solid.
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