5-Bromonicotinamide → 5-Azidonicotinamide

Participants

Reaction Steps

A solution of 5-bromonicotinamide (100 mg, 0.5 mmol), sodium azide (65 mg, 1.0 mmol), CuI (19.5 mg, 0.05 mmol), (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (11 mg, 0.08 mmol) and sodium ascorbate (5.0 mg, 0.03 mmol) in EtOH (0.7 mL) and H2O (0.3 mL) was degassed for 5 min before heated at reflux for 1.0 h. After cooled to rt, the mixture was extracted with EtOAc. The organic layer was washed with brine and dried over Na2SO4. After removal of the solvent, the crude was purified by silica gel column chromatography eluting with gradient EtOAc in hexanes (0-100%) to give 97A. 1H NMR (400 MHz, Methanol-d4) δ ppm 7.96-8.05 (m, 1H) 8.44 (d, J=2.64 Hz, 1H) 8.79 (d, J=1.76 Hz, 1H).

Provenance & Evidence