(E)-trimethyl(2-(tributylstannyl)vinyl)silane → HCID 86668306, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 4-amino-6-chloro-5-fluoro-3-iodopicolinate (0.5 g, 1.513 mmol), (E)-trimethyl(2-(tributylstannyl)vinyl)silane (0.589 g, 1.513 mmol), and bis(triphenylphosphine)palladium(II) chloride (0.106 g, 0.151 mmol) were combined in dichloroethane (3 mL) and stirred at 70° C. overnight. The reaction mixture was concentrated onto celite then purified by flash chromatography (SiO2, hexanes/EtOAc gradient) to afford the title compound (285 mg, 0.941 mmol, 62.2% yield) as an orange solid: mp 103-105° C.; 1H NMR (400 MHz, CDCl3) δ 6.99 (d, J=19.8 Hz, 1H), 6.21 (d, J=19.9 Hz, 1H), 4.72 (s, 2H), 3.89 (s, 3H), 0.19 (s, 9H); 19F NMR (376 MHz, CDCl3) δ −139.10; ESIMS m/z 301 [(M−H)−].

Provenance & Evidence