5-(Chloromethyl)-2-(trifluoromethyl)pyridine → 6-(2-chlorophenyl)-7-(4-chlorophenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

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Reaction Steps

The title compound was prepared from 6-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (79 mg, 0.22 mmol) and 5-(chloromethyl)-2-(trifluoromethyl)pyridine (74 mg, 0.38 mmol) according to the procedures described for 2-(4-(trifluoromethyl)benzyl)-6-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (Example 2). The crude product was purified using a silica gel cartridge (12 g) eluting with a gradient of EtOAc (0-80%) in hexanes to obtain the desired product as a yellow foam, which was lyophilized in acetonitrile to afford 87 mg (76%) of the title compound as a yellow powder. LC/MS (method A): retention time=3.76 min, (M+H)+=516. 1H NMR (CDCl3, 400 MHz): δ 8.86 (s, 1H), 8.02 (d,J=8.3 Hz, 1H), 7.47 (m, 1H), 7.42 (s, 1H), 7.33 (m, 2H), 7.25 (m, 2H), 7.20 (d,J=8.8 Hz, 2H), 7.02 (d,J=8.8 Hz, 2H), 5.34 (s, 2H).

Provenance & Evidence