Potassium Carbonate → 6-(2-chlorophenyl)-7-(4-chlorophenyl)-2-(4,4,4-trifluorobutyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Participants

Reaction Conditions

Reaction Steps

A suspension of 6-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (20 mg, 0.056 mmol), 1,1,1-trifluoro-4-iodobutane (20 mg, 0.084 mmol) and solid K2CO3 (12 mg, 0.084 mmol) in anhydrous DMF (0.6 mL) was stirred at 80° C. for 1 h. Analysis by HPLC/MS indicated the reaction was not complete. Additional 1,1,1-trifluoro-4-iodobutane (12 mg, 0.084 mmol) was added, the reaction was allowed to continue at 80° C. for 30 min. After cooling to room temperature, the reaction mixture was diluted with water, and extracted with EtOAc (20 mL×2). The combined EtOAc extracts were washed with water, saturated aqueous NaCl, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified using a silica gel cartridge (12 g) eluting with a gradient of EtOAc (0-60%) in hexanes to yield a yellow oily product, which was lyophilized in acetonitrile to afford 19 mg (73%) of the title compound as a yellow powder. HPLC (method B): retention time=7.70 min. 1H NMR (CDCl3, 400 MHz): δ 7.45 (m, 2H), 7.35 (m, 2H), 7.25 (m, 1H), 7.20 (d,J=8.8 Hz, 2H), 7.04 (d,j=8.8 Hz, 2H), 4.17 (t,J=6.1 Hz, 2H), 2.17-2.25 (m, 4H).

Provenance & Evidence