Triphenylphosphine → HCID 11554163, compound

Participants

Reaction Steps

To a stirred solution of 6-(4-hydroxymethylpiperidin-1-yl)pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (0.275 g, 0.90 mmol) in THF (10 mL) was added 2-hydroxybenzotrifluoride (0.178 g, 1.10 mmol), triphenylphosphine (0.289 g, 1.100 mmol) and diethyl azocarboxylate (0.5 mL, 1.10 mmol). The resulting mixture was stirred at ambient temperature for 18 hours. The solvent was removed in vacuo and the obtained crude product was purified by column chromatography to yield the title compound in 40% yield (0.035 g). 1H NMR (300 MHz, CDCl3) δ 7.98 (d, J=9.9 Hz, 2H), 7.54 (d, J=7.9 Hz, 1H), 7.47-7.42 (m, 1H), 6.99-6.92 (m, 3H), 4.57-4.53 (m, 2H), 3.89 (d, J=5.9 Hz, 2H), 3.56-3.49 (m, 2H), 3.11-3.02 (m, 2H), 2.25-2.15 (m, 1H), 2.01-1.97 (m, 2H), 1.52-1.41 (m, 2H), 1.27-1.20 (m, 2H), 0.75-0.68 (m, 1H), 0.47-0.41 (m, 2H), 0.09-0.05 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 163.3, 160.0, 156.7, 144.3, 133.3, 127.2, 127.1, 126.8, 125.5, 120.1, 112.5, 112.2, 72.6, 44.9, 39.6, 36.1, 34.6, 28.2, 8.7, 4.2. MS (ES+) m/z 449 (M+1).

Provenance & Evidence