Trimethylsilylacetylene → Methyl 4-(acetylamino)-2-chloro-5-[(trimethylsilyl)ethynyl]benzoate
Reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8](I)[C:7]([NH:11][C:12](=[O:14])[CH3:13])=[CH:6][C:5]=1[Cl:15].[C:17]([Si:19]([CH3:22])([CH3:21])[CH3:20])#[CH:18]>ClCCl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:18]#[C:17][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:7]([NH:11][C:12](=[O:14])[CH3:13])=[CH:6][C:5]=1[Cl:15]Participants
4
Procedure
To a stirred solution of 2-Chloro-4-acetamido-5-iodobenzoic acid methyl ester (2.5 g, 2.8 mmol) in dichloromethane (15.0 mL) were cuprous iodide (0.135 g, 0.71 mmol) and dichloro(bistriphenylphosphine)palladium(II) (0.25 g, 0.31 mmol). The mixture was cooled in an ice bath and added ethynyltrimethylsilane (0.825 g, 8.4 mmol). The resulting mixture was stirred under nitrogen at room temperature for 16 h. The mixture was diluted with dichloromethane (15.0 mL), washed with 5% citric acid, followed by water and dried (MgSO4). After the removal of the solvent, mixture was purified by silica gel flash chromatography using 20% ethyl acetate in heptane to afford the title compound as a light brown powder (1.9 g, 86%), m/z=252 (MH+—SiMe3).