Cesium carbonate → Ethyl 7-hydroxy-3-(4-methoxyphenyl)-4-phenylisoxazolo[4,5-c]pyridine-6-carboxylate

Participants

Reaction Steps

Ethyl 7-hydroxy-4-iodo-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate (200 mg, 0.45 mmol), phenylboronic acid (111 mg, 0.91 mmol), Pd(PPh3)4 (105 mg, 0.091 mmol) and cesium carbonate (444 mg, 1.36 mmol) were added to a flask and the flask evacuated. After refilling with nitrogen, 3 mL of 1,2-dimethoxyethane was added and the resulting suspension was refluxed for 16 h. The reaction mixture diluted with EtOAc (50 mL) and the solid was filtered. The solid was added to a mixture of 10% hydrochloric acid and extracted several times with EtOAc. The combined organic layer was dried over MgSO4 and concentrated, and the residue was purified flash chromatography (0-40% EtOAc/hexanes) to afford 68 mg of the title compound. MS: (+) m/z 391.41 (M+1).

Provenance & Evidence