Ethylene carbonate → 2-(4-{1-[3-(Trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenoxy)ethanol

Participants

Reaction Conditions

Reaction Steps

1,3-Dioxolan-2-one (1093 mg, 12.41 mmol) was added to 4-{1-[3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenol (907 mg, 2.48 mmol) and potassium carbonate (686 mg, 4.97 mmol) in DMF (10 mL). The resulting mixture was stirred at 80° C. for 16 hours. The reaction mixture was evaporated to dryness, the residue redissolved in DCM (100 mL) and the solution washed with water (100 mL). The aqueous washings were re-extracted with DCM (100 mL), then the combined organic phases were washed with saturated brine (50 mL), dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 2% MeOH in EtOAc. Pure fractions were evaporated to dryness to afford 2-(4-{1-[3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl}phenoxy)ethanol (695 mg, 68%).

Provenance & Evidence