1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59406417, compound

Participants

Reaction Steps

To a solution of [2-(4-methanesulfonyl-phenyl)-2H-pyrazol-3-yl]-methanol (4 mmol) and diphenylphosphoryl azide (0.95 mL, 4.4 mmol, 1.1 equiv) in THF (10 mL) at rt was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.6 mL, 4.4 mmol, 1.2 equiv). The resulting solution was stirred overnight, concentrated and chromatographically purified (15% ethyl acetate in hexanes) to give 5-azidomethyl-1-(4-methanesulfonyl-phenyl)-1H-pyrazole (0.344 g, 31% based on 4-(methylsulfonyl)phenylhydrazine hydrochloride, LCMS: (MH)+=278.0 (rt=1.36 min) and 3-azidomethyl-1-(4-methanesulfonyl-phenyl)-1H-pyrazole (75 mg, 7% based on 4-(methylsulfonyl)phenylhydrazine hydrochloride, LCMS: (MH)+=278.0 (rt=1.48 min)).

Provenance & Evidence