Potassium Carbonate → 5-Bromo-6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]-pyridine-3-sulfonic acid (2-cyclopropylethyl)amide

Participants

Reaction Steps

To a stirred solution of 5-bromo-6-chloro-pyridine-3-sulfonic acid (2-cyclopropylethyl)amide (0.432 g, 1.272 mmol) in dioxane (15.0 mL) was added (5-fluoro-2-trifluoromethylphenyl)piperazin-1-yl-methanone (0.386 g, 1.399 mmol), potassium carbonate (0.703 g, 5.080 mmol) and tetrabutyl ammonium bromide (0.042 g, 0.130 mmol). The resulting mixture was stirred at reflux for 48 h, filtered and then concentrated in vacuo. The crude product was purified by column chromatography, eluting with a solvent gradient of 35% ethyl acetate and 65% hexane to yield the desired product (0.235 g, 32%). 1H NMR (300 MHz, CDCl3) δ 8.59-8.58, 8.16-8.15, 7.74-7.69, 7.24-7.18, 7.08-7.04, 4.97-4.93, 4.03-3.85, 3.60-3.55, 3.43-3.33, 3.07-2.99, 1.41-1.34, 0.60-0.53, 0.43-0.37, 0.025-0.015. 13C NMR (75 MHz, CDCl3) δ166.1, 162.6, 145.4, 141.1, 130.5, 129.6, 129.5, 116.7, 116.4, 114.9, 114.7, 110.3, 48.8, 48.6, 46.9, 43.5, 41.6, 34.5, 8.2, 4.2. MS (ES+) m/z 581 (M+1).

Provenance & Evidence