Morpholine → 2-((7-Fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)oxy)-4-(4-morpholinyl)benzonitrile

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Reaction Steps

Prepared according to general Procedure H using 4-bromo-2-(7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yloxy)benzonitrile (70 mg, 0.16 mmol), tris(dibenzylideneacetone)dipalladium(0) (7.4 mg, 0.008 mmol), X-Phos (7.7 mg, 0.016 mmol), morpholine (28 mg, 0.32 mmol) and sodium tert-butoxide (31 mg, 0.32 mmol) in toluene (6.9 mL) and heating at reflux for 2 h. After purification 2-((7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)oxy)-4-(4-morpholinyl)benzonitrile was obtained. 1H NMR (400 MHz, chloroform-d) δ ppm 8.68-8.78 (1H, m), 7.86-7.95 (3H, m), 7.82 (1H, dd, J=10.0, 2.5 Hz), 7.57 (1H, d, J=8.6 Hz), 7.41 (1H, ddd, J=6.7, 4.6, 2.3 Hz), 7.30-7.36 (1H, m), 6.56 (1H, dd, J=9.0, 2.3 Hz), 5.83 (1H, d, J=2.3 Hz), 3.69 (4H, dd, J=6.1, 3.7 Hz), 2.90-3.10 (4H, m), 2.30-2.46 (3H, s). Mass Spectrum (ESI) m/e=441.0 (M+1).

Provenance & Evidence