p-Toluenesulfonic acid → Methyl 2-(2-fluoro-4-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxylate

Participants

Reaction Conditions

Reaction Steps

Methyl 3-(2-fluoro-4-(pyridin-4-yl)benzamido)-2-hydroxybenzoate (2.50 g, 6.83 mmol) and 4-methylbenzenesulfonic acid (3.25 g, 17 mmol) were added to toluene (50 mL) and the mixture was stirred at 118° C. 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) to obtain methyl 2-(2-fluoro-4-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxylate as white solid (500 mg, yield 21%). LC-MS (ESI) m/z: 349 (M+1)+.

Provenance & Evidence