Tributylvinyltin → Methyl 4-amino-5-fluoro-3-methoxy-6-vinylpicolinate

Participants

Reaction Steps

A mixture of methyl 4-amino-6-chloro-5-fluoro-3-methoxypicolinate (405 mg, 1.73 mmol), tributyl(vinyl)stannane (1.097 g, 3.46 mmol), and PdCl2(PPh3)2 (181 mg, 0.26 mmol) in 1,2-dichloroethane (3.5 mL) was heated at 120° C. in a Biotage microwave for 30 min Column chromatography (0-40% EtOAc/hexanes) of the crude reaction mixture provided the title compound as a yellow oil (0.38 g, 97%): 1H NMR (400 MHz, CDCl3) δ 6.88 (ddd, J=17.5, 11.1, 1.4 Hz, 1H), 6.33 (dd, J=17.5, 1.6 Hz, 1H), 5.57 (ddd, J=11.1, 1.6, 0.7 Hz, 1H), 4.47 (s, 2H), 3.97 (s, 3H), 3.91 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −143.2; ESIMS m/z 227 ([M+H]+).

Provenance & Evidence