Hydrochloric Acid → 3-(1-(2,3-difluorophenyl)-1H-imidazo[4,5-c]pyridin-2-yl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-tert-butyl-3-(1-(2,3-difluorophenyl)-1H-imidazo[4,5-c]pyridin-2-yl)pyridin-2-amine (1.5 g, 3.95 mmol) in methanol (7.0 mL) was added 6N aq. HCl at room temperature and the mixture heated at reflux for 5 hr. After cooling to 0° C., the pH of the solution was adjusted to pH 8-9 with 2N aq. NaOH solution (150 mL). The resulting precipitate was filtered off and dissolved in EtOAc (300 mL). The combined organics were washed with water (3×100 mL), brine (100 mL), and dried (Na2SO4). Filtration and evaporation of solvent in vacuo gave a solid, which was triturated with petroleum ether (3×20 mL) to give 3-(1-(2,3-difluorophenyl)-1H-imidazo[4,5-c]pyridin-2-yl)pyridin-2-amine (0.9 g, 75% yield) as a light yellow solid; LC-MS: 324.0 (M+H).

Provenance & Evidence