Benzyl Alcohol → Benzyl (5-bromopyridin-3-yl)carbamate

Participants

Reaction Steps

A mixture of 5-bromonicotinic acid (1.00 g, 4.95 mmol) and N-methylmorpholine (0.60 mL, 5.445 mmol) in anhydrous 1,2-dichloroethane (20 mL) was stirred under a nitrogen atmosphere for 10 minutes at room temperature. Diphenyl phosphoryl azide (1.17 mL, 5.445 mmol) was then added dropwise and the reaction stirred for 30 minutes at the same temperature. The reaction was then slowly heated to 75° C. over a 20-minute period and was maintained at this temperature for 1 hour. Benzyl alcohol (0.77 mL, 7.434 mmol) and cuprous chloride (15 mg) were added and the reaction was refluxed for 3 hours. The reaction was then cooled to room temperature and the solvent removed by rotary evaporation in vacuo. Purification by silica gel chromatography eluting with a gradient of 12% and 20% ethyl acetate/methylene chloride afforded the title compound as a white solid (524 mg, 34%).

Provenance & Evidence