(E)-trimethyl(2-(tributylstannyl)vinyl)silane → HCID 70497312, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 4-amino-6-ethyl-5-fluoro-3-iodopicolinate (270 mg, 0.833 mmol) and bis(triphenylphosphine)palladium(II) dichloride (58.5 mg, 0.083 mmol) were combined in a microwave reactor vessel. (E)-trimethyl(2-(tributylstannyl)vinyl)silane (649 mg, 1.666 mmol) dissolved in dichloroethane (0.8 mL) was added and the reaction mixture was heated at 120° C. for 30 min a microwave reactor. The cooled reaction mixture was diluted with ethyl acetate and water. The aqueous phase was extracted three more times with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered, and concentrated on to silica. The product was purifed by flash chromatography (SiO2, 0-30% EtOAc:Hex gradient) to provide the title compound as an off-white solid (143 mg, 0.482 mmol, 57.9% yield): 1H NMR (400 MHz, DMSO-d6) δ 0.14 (s, 9H), 1.16 (t, J=7.6 Hz, 3H), 2.65 (qd, J=7.6, 2.6 Hz, 2H), 3.71 (s, 3H), 5.99 (d, J=19.3 Hz, 1H), 6.25 (s, 2H), 6.84 (d, J=19.2 Hz, 1H); 19F NMR (376 MHz, DMSO-d6) δ −148.85; ESIMS m/z 297 ([M+H]+), 295 ([M−H]−).

Provenance & Evidence