1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(Azidomethyl)quinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of quinolin-7-ylmethanol (1.2 g, 7.2 mmol) and diphenylphosphonic azide (3.8 mL, 17 mmol) was dissolved in toluene (20 mL) and methylene chloride (6 mL). The mixture was cooled to 0° C. and neat 1,8-diazabicyclo[5.4.0]undec-7-ene (2.6 mL, 17 mmol) was added. The reaction was stirred for 30 minutes at 0° C. and then reacted at room temperature for 2 h. The mixture was diluted with CH2Cl2 (100 mL) and washed with water (100 mL×2). The organic layer was concentrated in vacuo and purified by silica gel chromatography (0-100% EtOAc/hexane) to afford a colorless oil.

Provenance & Evidence