Sodium hydride → 4-[3,3-Dimethyl-6-(Morpholin-4-Yl)-2,3-Dihydro-1h-Indol-1-Yl]-7-Fluoro-3-Methyl-2-(Pyridin-3-Yl)quinoline

Participants

Reaction Steps

Prepared according to procedure M using 4-chloro-7-fluoro-3-methyl-2-(pyridin-3-yl)quinoline (250 mg, 0.92 mmol), 4-(3,3-dimethylindolin-6-yl)morpholine (213 mg, 0.92 mmol) and sodium hydride (44 mg, 1.833 mmol) in DMF (2.0 mL) and heating the reaction at 120° C. for 3 h. After purification 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-7-fluoro-3-methyl-2-(3-pyridinyl)-quinoline was obtained as a yellow film. 1H NMR (400 MHz, chloroform-d) δ ppm 8.90 (1H, br. s.), 8.66-8.81 (1H, m), 8.00 (1H, dt, J=7.8, 2.0 Hz), 7.89 (1H, dd, J=9.4, 5.9 Hz), 7.81 (1H, dd, J=10.0, 2.5 Hz), 7.48 (1H, dd, J=7.8, 4.7 Hz), 7.23-7.30 (1H, m), 7.09 (1H, d, J=8.2 Hz), 6.34 (1H, dd, J=8.2, 2.3 Hz), 5.61 (1H, d, J=2.3 Hz), 3.68-3.81 (6H, m), 2.90-3.02 (4H, m), 2.30 (3H, s), 1.52 (3H, s), 1.47 (3H, s). Mass Spectrum (ESI) m/e=469 (M+1).

Provenance & Evidence