p-Toluenesulfonyl azide → HCID 86662263, compound

Participants

Reaction Conditions

Reaction Steps

To a −78° C. solution of 5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (0.215 g, 0.62 mmol) in 3 mL of THF (3 mL) was added 1.67 M BuLi (0.45 mL, 0.75 mmol). The reaction was stirred at −78° C. for 30 min and then tosyl azide (0.160 g, 0.81 mmol) in THF (0.5 mL) was added dropwise. The reaction was stirred at −78° C. for 1 h when it was determined to be complete by LCMS. The reaction was quenched at −78° C. with pH 7 buffer and allowed to warm to room temperature. The mixture was extracted with DCM (3×10 mL) and dried with MgSO4. The residue was purified by column chromatography using Hex:EtOAc as eluents to afford 2-azido-5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (131 mg) as a yellow oil. MS (EI) m/z 386 [M+H]+.

Provenance & Evidence