Sodium Carbonate → HCID 67128330, compound

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A solution of 3-bromo-6-(4-chloro-2-fluoro-3-methoxyphenyl)-4-[(E)-methylsulfonyloximino]-1,4,5,6-tetrahydropyridine-2-carboxylic acid methyl ester (23, 900 mg, 1.856 mmol) in glacial acetic acid (4.6 mL) was heated at 150° C. for 5 min in a Biotage microwave. After cooling to ambient temperature the reaction mixture was diluted with H2O and the pH was made neutral with a saturated solution of Na2CO3. The resulting mixture was extracted 3 times with ethyl acetate. The combined organic extracts were washed with brine, dried with Na2SO4, filtered and concentrated in vacuo. Silica gel column chromatography (20% EtOAc/pentane) gave 4-amino-3-bromo-6-(4-chloro-2-fluorophenyl)pyridine-2-carboxylic acid methyl ester (41; 0.60 g, 83%) as a light brown solid: mp 148-149° C.; 1H NMR (300 MHz, CDCl3) δ 7.65 (dd, J=8.6, 7.7 Hz, 1H), 7.26-7.20 (m, 1H), 7.14 (d, J=1.8 Hz, 1H), 4.91 (s, 2H), 3.99 (s, 3H), 3.97 (d, J=0.9 Hz, 3H); HRMS-ESI (m/z): calcd for C14H11BrClFN2O3, 387.962. found, 387.963.

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