1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(azidomethyl)-1H-indole

Participants

Reaction Steps

To a solution of 1H-indole-4-methanol (Example 17; 71 mg, 0.48 mmol) in tetrahydrofuran (1 mL) at 0° C. was added diphenylphosphoryl azide (156 μL, 0.72 mmol) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (87.4 μL, 0.58 mmol). The cooling bath was removed and the solution was allowed to stir for 5 h. After the solvent was evaporated, ethyl acetate was added and the solution was washed with 1N hydrochloric acid solution and brine, dried (MgSO4), filtered and concentrated. The residual material was chromatographed over silica gel (12% ethyl acetateihexanes) to give 4-(azidomethyl)-1H-indole (1.496 g, 88% yield) as an oil.

Provenance & Evidence