Phosphorus oxychloride → HCID 59233097, compound

Participants

Reaction Steps

A solution of N′-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)propanehydrazide (5.0 g, 14.02 mmol) and phosphoryl trichloride (100 mL, 1073 mmol) was stirred at 90° C. for 5 hrs. The reaction was cooled, stripped to dryness, and the resulting material was reconstituted in a mixture of EtOAc and saturated NaHCO3 (400 mL, 1:1)). The organic phase was isolated, washed with saturated NaHCO3 (1×100 mL), and dried over MgSO4. The organic phase was removed via rotary evaporation to provide the title compound, 6-bromo-3-(1-(6-chloropyridazin-3-yl)ethyl)-[1,2,4]triazolo[4,3-a]pyridine 48D (2.2 g, 6.50 mmol, 46.3% yield). This material was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.86 (d, J=7.07 Hz, 3 H) 5.27 (d, J=7.33 Hz, 1 H) 7.49 (dd, J=9.60, 1.77 Hz, 1 H) 7.78 (dd, J=9.85, 1.01 Hz, 1 H) 7.94 (s, 2 H) 8.79 (s, 1 H). ESI-MS:m/z 339.1 (M+H)+.

Provenance & Evidence