Anisole → 6-((6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)difluoromethyl)pyridazin-3-amine

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Reaction Steps

A solution of 6-((6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)difluoromethyl)-N-(2,4-dimethoxybenzyl)pyridazin-3-amine (16.5 g, 33.6 mmol) and anisole (5.45 g, 50.4 mmol) in TFA (150 mL) was stirred at 70° C. for 30 min. The reaction was concentrated to dryness via rotary evaporation and the resulting residue was sonicated in a solution of Et2O/NaHCO3 (pH=7). The resulting solid was collected by filtration, rinsed with water and then Et2O, and dried in vacuum over P2O5 to provide the title compound, 6-((6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)difluoromethyl)pyridazin-3-amine 45H (11.0 g, 32.2 mmol, 96%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.14 (d, J=9.35 Hz, 1 H) 7.71 (dd, J=9.85, 1.77 Hz, 1 H) 7.92 (d, J=9.35 Hz, 1 H) 7.92 (d, J=10.20 Hz, 1 H) 8.02 (d, J=10.20, 1 H) 8.74 (s, 1 H). ESI-MS:m/z 340.9 (M+H)+.

Provenance & Evidence