Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:15][Si:16]([C:19]#[CH:20])([CH3:18])[CH3:17].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[N+:12]([C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([C:20]#[C:19][Si:16]([CH3:18])([CH3:17])[CH3:15])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])([O-:14])=[O:13]
A solution of methyl 3-bromo-5-nitrobenzoate (0.331 g, 1.27 mmol), (trimethylsilyl)acetylene (0.27 mL, 1.9 mmol), bis(triphenylphosphine)palladium(II) chloride (45 mg, 0.064 mmol), copper(I) iodide (19 mg, 0.10 mmol) and triethylamine (0.26 mL, 1.9 mol) in DMF (5 mL) was stirred at room temperature overnight. The solution was diluted with ethyl acetate and 1 N HCl. The aqueous layer was extracted with ethyl acetate once, and the combined organic solutions were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography (10% ethyl acetate in hexanes) to give the desired product (310 mg, 88%). LCMS for C13H16NO4Si (M+H)+: m/z=278.1.
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