反应详情

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).

1. temperaturebefore heated
2. temperatureat reflux for 1.0 h
3. extractionthe mixture was extracted with EtOAc
4. washThe organic layer was washed with brine
5. dry with materialdried over Na2SO4
6. customAfter removal of the solvent
7. customthe crude was purified by silica gel column chromatography
8. washeluting with gradient EtOAc in hexanes (0-100%)