Diisopropylamine → HCID 67532332, compound

Participants

Reaction Steps

Ethyl 7-hydroxy-4-iodo-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (500 mg, 1.22 mmol), copper iodide (93 mg, 0.49 mmol), and PdCl2(PPh3)2 (171 mg, 0.24 mmol) were added to a flask and the flask evacuated. After refilling with nitrogen, THF (20 mL), diisopropylamine (1 mL) and TMS acetylene (0.35 mL, 2.44 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 (0-100% CH2Cl2/hexanes) to afford 405 mg of the title compound. MS: (+) m/z 381.35 (M+1).

Provenance & Evidence