Ammonium → HCID 18977010, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5 ml. of 2.5M butyllithium in hexane, diluted further with 10 ml. of hexane, was chilled to -90° C. This was treated by dropwise addition with 1.97 g (12.5 mmoles) of 3-bromopyridine in 10 ml. of hexane. The yellow slurry was stirred at -60° C. for 1 hr. and then treated by dropwise addition with 0.70 g (6.2 mmoles) of 1,2-diazidoethane. The solution remained yellow, and was stirred at room temperature overnight. The reaction mixture was then treated with ammonium buffer and the solvents were removed in vacuo. The residue was treated with 50 ml. of diethylether and 10 ml. of water overnight. The residual powder was virtually pure product in a yield of 120 mg (pale orange). The product migrated as a single spot on thin layer chromatography and the nmr and mass spectra were fully consistent with the structure.

Provenance & Evidence