C([SiH](CC)CC)C.[Cl:8][C:9]1[CH:32]=[CH:31][C:12]([CH2:13][N:14]2[CH:19]=[C:18]([CH:20](O)[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=3)[CH:17]=[CH:16][C:15]2=[O:30])=[CH:11][CH:10]=1.CO>C(O)(C(F)(F)F)=O>[CH3:28][O:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][C:18]1[CH:17]=[CH:16][C:15](=[O:30])[N:14]([CH2:13][C:12]2[CH:11]=[CH:10][C:9]([Cl:8])=[CH:32][CH:31]=2)[CH:19]=1According to Scheme 7 Method D: Triethylsilane (3 eq, 0.84 mmol, 0.10 g) was added to a solution of 1-(4-chlorobenzyl)-5-(hydroxy(3-methoxyphenyl)methyl)pyridin-2(1H)-one (1 eq, 0.28 mmol, 0.10 g, Example 41) in TFA (2 mL). The mixture was stirred 1 hour at room temperature. Upon completion, MeOH was added and the solution was evaporated. The crude residue was partitioned between water and CH2Cl2. The aqueous layer was extracted with CH2Cl2. The combined organic layers were successively washed with brine, dried over MgSO4 and concentrated under vacuum to afford the crude product. Purification by flash chromatography (AIT Flashsmart prepacked column 10 g SiO2) (CH2Cl2/AcOEt 95/5 to 90/10) of the crude product afford the title compound 5-(3-methoxybenzyl)-1-(4-chlorobenzyl)pyridin-2(1H)-one (0.20 mmol, 0.07 g, 71%) as a yellow oil.
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