Diisopropylamine → HCID 67529979, compound

Participants

Reaction Steps

Ethyl 7-hydroxy-4-iodo-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (300 mg, 0.73 mmol), copper iodide (56 mg, 0.29 mmol), and PdCl2(PPh3)2 (103 mg, 0.15 mmol) were added to a flask and the flask evacuated. After refilling with nitrogen, THF (5 mL), diisopropylamine (0.6 mL) and phenylacetylene (0.1 mL, 0.95 mmol) were added and the resulting mixture was stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was partitioned between 25 mL of 1M hydrochloric acid and 25 mL of EtOAc. The aqueous layer was extracted with additional EtOAc and the combined organic layer was dried over MgSO4 and concentrated. The residue was purified flash chromatography (0-40% EtOAc/hexanes) to afford 195 mg of the title compound. MS: (+) m/z 385.29 (M+1).

Provenance & Evidence