Trifluoroacetic acid → N-(2-(2,5-difluorophenyl)-5-methylpyridin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine

Participants

Reaction Conditions

Reaction Steps

N-(2-(2,5-Difluorophenyl)-5-methylpyridin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-7-amine and N-(2-(2,5-difluorophenyl)-5-methylpyridin-4-yl)-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridin-7-amine and trifluoroacetic acid (35 mL) were combined and heated at 70° C. for 3 hours, then cooled to room temperature and stirred overnight. The reaction mixture was then concentrated in vacuo to give a residue which was dissolved in dichloromethane (75 mL) and was poured into a saturated solution of sodium bicarbonate (50 mL) to give a solid which was collected by filtration and dissolved in ethyl acetate (500 mL), washed with brine (50 mL), dried over magnesium sulfate, filtered and concentrated to give N-(2-(2,5-difluorophenyl)-5-methylpyridin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.37 (3H, s) 7.09 (1H, d, J=4.80 Hz) 7.26-7.36 (2H, m) 7.50 (1H, s) 7.75 (1H, ddd, J=9.54, 6.13, 3.28 Hz) 8.24 (1H, d, J=1.26 Hz) 8.35 (1H, d, J=5.05 Hz) 8.43 (1H, s) 8.50 (1H, s) 13.03 (1H, s). MS [M+H] found 337.3.

Provenance & Evidence