Hydrochloric Acid → Methyl 2-(2-methyl-4-(trifluoromethyl)phenyl)isonicotinate hydrochloride

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Reaction Conditions

Reaction Steps

Potassium carbonate (2.66 g, 19.23 mmol), methyl 2-chloroisonicotinate (5.5 g, 32.05 mmol), 2-methyl-4-(trifluoromethyl)phenylboronic acid (8.50 g, 41.67 mmol), PdCl2 (dppf) (0.696 g, 0.96 mmol), and MeOH (50.3 mL) were split into three microwave vials and heated in a single node microwave reactor to 100° C. for 20 min. Diluted with DCM, filtered and evaporated. Purified by flash chromatography using 5% EtOAc in heptane ->20% EtOAc over 10 CV at 280 nm. The residue was dissolved in ether and hydrogen chloride (4 M in dioxane, 8.01 mL, 32.05 mmol) was added and the solvents evaporated to yield methyl 2-(2-methyl-4-(trifluoromethyl)phenyl)isonicotinate hydrochloride (9.15 g, 86%) as a white solid. 1H NMR (400 MHz, cd3od) δ 2.41 (s, 3H), 4.03 (s, 3H), 7.63-7.76 (m, 3H), 8.27 (dd, 1H), 8.33 (dd, 1H), 8.99 (dd, 1H). MS m/z 296 (M+H)+

Provenance & Evidence