Tributylvinyltin → 3-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-5-vinylpyridazine

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To a solution of 5-chloro-3-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)pyridazine (23-2, 730 mg, 3.48 mmol, 1.0 eq.) in toluene (24 mL) were added tetrakis(triphenylphosphine)palladium(0) (200 mg, 0.17 mmol, 0.05 eq.) and tributyl(vinyl)tin (1.30 mL, 4.52 mmol, 1.3 eq.). The mixture was heated at 120° C. for 3 hours. The solvent was removed under reduced pressure and the resulting residue was purified by silica gel column chromatography (30% ethyl acetate in hexanes) to afford 3-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-5-vinylpyridazine (23-3) as a white solid. 1H NMR (300 MHz, CDCl3) δ 9.15 (d, 1H, J=1.8 Hz), 8.02 (d, 1H, J=1.8 Hz), 6.73 (dd, 1H, J=17.7, 10.8 Hz), 6.23 (d, 1H, J=17.7 Hz), 5.78 (d, 1H, J=10.8 Hz), 2.95 (s, 3H), 2.44 (s, 3H).

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