tert-Butanol → 2-(5-Chloro-2-fluorophenyl)-6-methylpyridin-4-amine

Participants

Reaction Steps

2-(5-Chloro-2-fluorophenyl)-6-methylisonicotinic acid (1.1 g, 4.14 mmol), diphenyl phosphorazidate (0.895 ml, 4.14 mmol), triethylamine (0.873 ml, 6.21 mmol), 2-methylpropan-2-ol (0.466 ml, 4.97 mmol) were combined in toluene (12.5 mL) and heated at reflux for 30 minutes, then cooled and concentrated to give a residue. The residue was purified by silica chromatography eluted using a step gradient (0-25% ethyl acetate/hexanes) to give the title compound as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.49 (s, 9H) 2.46 (s, 3H) 7.34-7.42 (m, 2H) 7.49-7.56 (m, 1H) 7.76 (s, 1H) 7.94 (dd, J=6.82, 2.78 Hz, 1H) 9.90 (s, 1H). ESI-MS: m/z 337.2 (M+H).

Provenance & Evidence