Tributylvinyltin → HCID 67457050, compound

Participants

Reaction Steps

To a solution of 3-(4-iodo-3-methylphenyl)-5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazole (1.45 g, 2.92 mmol) in dioxane (5 mL) in a sealed tube was added sequentially tributyl(vinyl)stannane (0.942 mL, 3.21 mmol) and lithium chloride (0.371 g, 8.75 mmol). The mixture was degassed under reduced pressure and charged with nitrogen (2×). To the mixture was added tetrakis(triphenylphosphine) palladium(0) (0.337 g, 0.292 mmol), and the mixture was stirred under a strong stream of nitrogen for 5 min. The reaction mixture was sealed, immersed in an oil bath at 100° C., and stirred overnight. The reaction mixture was diluted with ethyl acetate and filtered. The solid was rinsed with ethyl acetate (3×). The filtrate was concentrated, diluted with ether, and filtered under reduced pressure. HPLC indicated that the product was in the filtrate, which was concentrated under reduced pressure and purified by flash silica gel chromatography using a mixture of ethyl acetate in hexane (1%-2.5%) to give 3-(3-methyl-4-vinylphenyl)-5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazole (0.514 g, 1.294 mmol, 44.4% yield) as an white solid. The compound had an HPLC ret. time=3.85 min.−Column. CHROMOLITH® SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. MS M+1=398.0. 1H NMR (500 MHz, CDCl3) δ ppm 2.47 (s, 3H), 5.43-5.46 (m, 1H), 7.00 (dd, J=17.34, 10.96 Hz, 1H), 7.53-7.62 (m, 3H) 7.65 (d, J=8.32 Hz, 1H), 7.69 (d, J=6.94 Hz, 2H), and 7.99-8.04 (m, 2H).

Provenance & Evidence