Benzyl azide → HCID 67530374, compound

Participants

Reaction Steps

Ethyl 4-ethynyl-7-hydroxy-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (185 mg, 0.60 mmol), benzyl azide (0.087 mL, 0.66 mmol), CuSO4-5H2O (7.5 mg, 0.03 mmol), and sodium ascorbate (18 mg, 0.09 mmol) were added to a mixture of CH2Cl2 (2 mL) and water (2 mL). The mixture was stirred at room temperature for 16 h. Another equiv. of benzyl azide was added, and the mixture was stirred for an additional 16 h. The mixture was diluted with CH2Cl2 (20 mL) and water (20 mL). The aqueous layer was extracted with additional CH2Cl2 and the combined organic layer was dried over MgSO4 and concentrated. The crude product was purified twice by flash chromatography (first with 0-100% EtOAc/hexanes, then with 0-50% CH2Cl2/EtOAc) to afford 100 mg of the title compound. MS: (+) m/z 442.33 (M+1).

Provenance & Evidence