Potassium Carbonate → Methyl 6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carboxylate

Participants

Reaction Steps

A mixture of methyl 6-chloropyridazine-3-carboxylate (500 mg, 0.2.9 mmol), 4-[2-(trifluoromethyl)phenoxy]piperidine (851 mg, 0.3.5 mmol), potassium carbonate (802 mg, 5.8 mmol) and tetrabutylammonium iodide (20 mg, 0.06 mmol) in dioxane (30 mL) was refluxed for 24 h. After cooling, the mixture was filtered through celite, washed with EtOAc and concentrated. CombiFlash chromatography (40 g, 60-90% EtOAc in hexanes in 20 min, 35 mL/min, 18 mL/fraction) gave the title compound as a white solid. 1H NMR (400 MHz, acetone-d6): δ 1.93-1.99 (m, 2H), 2.14-2.20 (m, 2H), 3.93 (s, 3H), 3.97-4.09 (m, 4H), 5.03-5.07 (m, 1H), 7.13 (t, 1H), 7.31 (d, 1H), 7.40 (d, 1H), 7.65 (dd, 2H), 7.89 (d, 1H).

Provenance & Evidence