Tributyl(prop-1-yn-1-yl)stannane → (2-Chloro-phenyl)-(2-prop-1-ynyl-pyridin-3-yl)-methanone

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Reaction Steps

Dissolve (2-bromo-pyridin-3-yl)-(2-chloro-phenyl)-methanone (18.0 g, 60.8 mmol) in toluene (600 mL) and purge the solution with nitrogen. After 10 minutes., add tributyl(1-propynyl)tin (22.2 mL, 72.9 mmol) followed by tetrakis(triphenylphosphine)palladium (2.10 g, 1.82 mmol) and heat the mixture to reflux temperature. After 2 hours, cool the mixture to room temperature and concentrate. Purification by flash chromatography on silica gel eluting with hexanes:ethyl acetate (5:1 to 2:1) gives the title compound: m.p.=45-49° C.; mass spectrum (m/e): 256 (M+H+); 1H NMR (CDCl3) δ 8.67-8.68 (m, 1H), 7.95-7.98 (m, 1H), 7.32-7.55 (m, 5H), 1.74 (s, 3H); HPLC 98.4%; TLC (Silica, 2:1 Hexanes:Ethyl Acetate) Rf 0.20.

Provenance & Evidence