Potassium Carbonate → 4-(Trifluoromethyl)benzyl-8-chloro-7-(4-chlorophenyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one

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Reaction Conditions

Reaction Steps

To a solution of 8-chloro-7-(4-chlorophenyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one (0.54 g, 1.91 mmol), prepared as described in Example 354, in DMF (5 mL) at RT was added K2CO3 (0.40 g, 2.87 mmol) and 2-(trifluoromethyl)benzyl bromide (0.595 g, 2.49 mmol). The reaction mixture was heated at 55° C. for 4 h. After this time, the mixture was diluted with EtOAc (150 mL). The resultant solution was washed with water and saturated aqueous NaCl. The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using hexanes:EtOAc (2:1) to afford 0.74 g of the title compound, 2-(4-(trifluoromethyl)benzyl-8-chloro-7-(4-chloro-phenyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one as a yellow solid. HPLC RT: 3.84 min; MS, M+H=439. 1H NMR (CDCl3): δ 8.08 (s, 1H), 7.44-7.61 (m, 8H), 5.30 (s, 2H).

Provenance & Evidence