[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[CH3:9][O:10][C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1>[CH3:1][N:2]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]([O:10][CH3:9])=[O:20])=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=12-Methylaminopyridine (1.0 mmol) and methyl-4-formylbenzoate (1.0 mmol) were mixed in THF (2 mL) and dibutyltin dichloride (0.1 mmol) was added. After stirring at RT for 10 minutes, phenylsilane (1.1 mmol) was added and the reaction mixture allowed to stir at room temperature for a further 17 h. The reaction mixture was then concentrated by N2 stream and the residue purified by flash chromatography (silica gel, heptane:EtOAc) to give methyl 4-[methyl(pyridin-2-yl)amino]methylbenzoate: m/z=257 in MS ES+ as a yellow oil which was used directly in the subsequent step.
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