p-Toluenesulfonic acid → HCID 66621211, compound

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Reaction Steps

Methyl 2-hydroxy-3-(4-(pyridin-3-yl)benzamido)benzoate (1.04 g, 3 mmol) and 4-methylbenzenesulfonic acid (1.2 g, 6 mmol) were added to toluene (20 mL) and the mixture was stirred under reflux for 2 days. The resulting mixture was extracted with ethyl acetate (100 mL×4) and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 20:1 to 10:1). 150 mg of methyl 2-(4-(pyridin-3-yl)phenyl)benzo[d]oxazole-7-carboxylate as a solid was obtained, yield: 15%. 1H-NMR (400 MHz, DMSO-d6) δ 4.02 (s, 3H), 7.55-7.59 (m, 1H), 7.97-7.99 (m, 1H), 8.04-8.06 (d, J=8.0 Hz, 2H), 8.13-8.15 (m, 1H), 8.21-8.24 (m, 1H), 8.33-8.35 (d, J=8.2 Hz, 2H), 8.65-8.66 (m, 1H), 9.03-9.04 (d, J=2.0 Hz, 1H); LC-MS (ESI) m/z: 331 (M+1)+.

Provenance & Evidence