Sodium hydride → 4-(3,3-Dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-5-fluoro-3-methyl-2-(2-pyridinyl)quinoline

Participants

Reaction Conditions

Reaction Steps

Prepared according to procedure M using 3,3-dimethyl-6-morpholinoindoline (348 mg, 1496 μmol), 4-chloro-5-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (340 mg, 1247 μmol) in DMF (12 mL), and sodium hydride (72 mg, 2992 μmol) and heating at 130° C. overnight. After purification 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-5-fluoro-3-methyl-2-(2-pyridinyl)quinoline was obtained as a yellow film. 1H NMR (400 MHz, chloroform-d) δ ppm 8.76 (1H, dd, J=3.5, 1.2 Hz), 8.02 (1H, d, J=8.2 Hz), 7.83-7.96 (2H, m), 7.60 (1H, td, J=8.1, 5.3 Hz), 7.40 (1H, ddd, J=7.0, 5.1, 2.0 Hz), 7.08-7.17 (1H, m), 7.04 (1H, d, J=8.2 Hz), 6.26 (1H, dd, J=8.0, 2.2 Hz), 5.50 (1H, d, J=2.3 Hz), 3.76-3.85 (1H, m), 3.60-3.76 (5H, m), 2.86-3.02 (4H, m), 2.42 (3H, s), 1.50 (3H, s), 1.44 (3H, s). Mass Spectrum (ESI) m/e=469 (M+1).

Provenance & Evidence