Tert-Butyl nitrite → HCID 57950691, compound

Participants

Reaction Conditions

Reaction Steps

Neat tert-butyl nitrite (670 μL, 5633 μmol) was added to a suspension of 5-aminoindazole (500 mg, 3755 μmol) (commercially available from VWR Chemical Catalog (Order Number AAAL06705-14)) in MeCN (7 mL) at 0° C. followed by dropwise addition of trimethylsilyl azide (598 μL 4506 μmol). The mixture was stirred at 0° C. for 5 minutes room temperature for 18 hours, and at 50° C. for 24 hours. The mixture was concentrated under reduced pressure, and the resulting brown residue was absorbed onto silica gel and purified by flash chromatography (silica gel, 2% to 6% MeOH/DCM) to provide 5-azido-1H-indazole (456 mg, 76%) as a golden solid. LCMS (API-ES) m/z: 160.1 (M+H+).

Provenance & Evidence