Methanol → Methyl 4-acetamido-6-(4-chloro-2-fluoro-3-methoxyphenyl)-3-methoxypicolinate

Participants

Reaction Steps

Methyl 4-acetamido-6-(4-chloro-2-fluoro-3-methoxyphenyl)-3-hydroxypicolinate (568 mg, 1.54 mmol), triphenylphosphine (404 mg, 1.54 mmol), diethyl azodicarboxylate (243 μL, 1.54 mmol), and CH3OH (94 μL, 2.31 mmol) were combined in THF and allowed to stir for 24 h. Flash chromatography (SiO2; 0-50% EtOAc/cyclohexane gradient) afforded the title compound as a yellow oil (255 mg, 43%): 1H NMR (400 MHz, CDCl3) δ 8.93 (d, J=1.6 Hz, 1H), 8.06 (s, 1H), 7.56 (dd, J=8.5, 7.7 Hz, 1H), 7.23 (dd, J=8.6, 1.7 Hz, 1H), 4.01 (s, 3H), 3.99 (d, J=1.0 Hz, 3H), 3.98 (s, 3H), 2.29 (s, 3H); ESIMS m/z 383 ([M+H]+).

Provenance & Evidence