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

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Reaction Steps

A mixture of 6-chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide (180 mg, 0.73 mmol), 4-[2-(trifluoromethyl)phenoxy]piperidine (150 mg, 0.67 mmol), potassium carbonate (184 mg, 1.33 mmol) and tetrabutylammonium iodide (7 mg, 0.02 mmol) in dioxane (10 mL) was refluxed for 2 days. After cooling, the mixture was diluted with EtOAc and filtered through celite. Solvent was removed in vacuo. Combi-Flash chromatography (10 g, 50-80% EtOAc in hexanes in 20 min, 20 mL/min, 18 mL/fraction) gave the title compound as a white powder. 1H NMR (500 MHz, acetone-d6): δ 0.11-0.13 (m, 2H), 0.45-0.49 (m, 2H), 0.76-0.84 (m, 1H), 1.56 (q, 2H), 2.13-2.20 (m, 4H), 3.52-3.56 (m, 2H), 3.91-3.97 (m, 2H), 4.00-4.06 (m, 2H), 5.01-5.05 (m, 1H), 7.12 (t, 1H), 7.37 (m, 2H), 7.61-7.67 (m, 2H), 7.92 (d, 1H), 8.24 (s, 1H); MS (+ESI) m/z 435 (MH+).

Provenance & Evidence