[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([NH2:14])[NH:11][N:10]=2)=[CH:5][CH:4]=1.[CH:15]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1)=O.[Sn](CCCC)(CCCC)(Cl)Cl.C1([SiH3])C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([NH:14][CH2:15][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=3)[NH:11][N:10]=2)=[CH:5][CH:4]=1A solution of amine 383 (720 mg, 3.79 mmol), methyl 4-formylbenzoate (745 mg, 4.54 mmol), and Bu2SnCl2 (230 mg, 0.76 mmol) in dry THF (5 mL) was stirred at room temperature for 2 hours. It was then treated with PhSiH3 (514 μL, 451 mg, 4.17 mmol) and allowed to stir for another hour at room temperature. The reaction mixture was quenched by addition of MeOH and vigorous stirring for 45 min. It was then concentrated in vacuo and the residue was purified by flash chromatography using the gradient 50-100% EtOAc in hexane to afford the title compound (672 mg, 52% yield). LRMS: (calc) 338.1; (found) 339.2 (M+H1)
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