(Z)-1-Ethoxy-2-(tributylstannyl)ethene → HCID 67261221, compound

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A mixture of 5-(2,4-difluorobenzyl)-1-(2-fluorobenzyl)-3-iodopyridin-2(1H)-one 5 (6.61 g, 14.5 mmol), bis(triphenylphosphine)palladium(II) chloride (1.02 g, 1.5 mmol), and ethoxyvinyl(tributyl)tin (10.81 g, 29.0 mmol) in anhydrous DMF (145 ml) was heated at 700 under argon condition for 1 h. DMF was distilled off and the resulting residue was dissolved in ethyl acetate (145 ml) and filtered through a pad of celite. The filtrate was stirred with 1N HCl (145 ml) for 15 min, washed with water (2×145 ml), brine (145 ml), dried over anhydrous sodium sulfate, and distilled off. The residue was purified by flash column chromatography on silica gel (hexanes:ethyl acetate, 80:20). Yield 4.21 g (78%). 1H NMR (CDCl3, 500 MHz): δ 7.98 (d, 1H, J=2.6 Hz), 7.49-7.44 (m, 2H), 7.35-7.30 (m, 1H), 7.16-7.07 (m, 3H), 6.85-6.78 (m, 2H), 5.17 (s, 2H), 3.71 (s, 2H), 2.67 (s, 3H). 13C NMR (CDCl3, 125 MHz): δ 197.6, 162.4, 162.1, 160.5, 160.4, 160.2, 144.4, 141.4, 131.4, 131.2, 130.4, 127.7, 124.6, 122.6, 122.1, 116.9, 115.6, 111.5, 104.1, 47.2, 30.9, 30.5.

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