Reaction Steps
A mixture of 3,3-difluoro-1-piperidin-4-yl-1,3-dihydroindol-2-one (0.180 g, 0.71 mmol), 6-chloropyridazine-3-carboxylic acid (3-cyclopropylpropyl)amide (0.160 g, 0.66 mmol), K2CO3 (0.150 g, 1.08 mmol) and n-Bu4NI (10 mg) in dioxane (10 mL) was heated to reflux overnight, then concentrated. The residue was purified by flash chromatography to yield the title compound as a white powder in 60% yield (0.183 g). m.p. 51-53° C. 1H NMR (300 MHz, CDCl3) δ 7.97 (d, J=9.3 Hz, 1H), 7.86 (s, br, 1H), 7.50 (d, J=6.6 Hz, 1H), 7.12-6.91 (m, 3H), 4.66 (d, J=12.9 Hz, 2H), 4.35 (s, br, 1H), 3.46-3.42 (m, 2H), 3.09 (t, J=12.9 Hz, 2H), 2.52-2.35 (m, 2H), 1.90 (d, J=11.4 Hz, 2H), 1.69-1.65 (m, 2H), 1.28-1.23 (m, 2H), 0.72-0.55 (m, 1H), 0.48-0.25 (m, 2H), 0.08-−0.07 (m, 2H.); 13C NMR (75 MHz, CDCl3) δ 165.1, 163.1, 159.7, 144.9, 142.4, 133.4, 127.0, 125.1, 123.7, 120.3, 112.3, 110.7, 106.9, 50.9, 44.6, 39.1, 35.1, 29.5, 28.3, 27.5, 26.1, 10.4, 4.4. MS (ES+) m/z 456.3 (M+1).
