Sodium hydride → 4-(3,3-Dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline

Participants

Reaction Conditions

Reaction Steps

Prepared according to procedure M using 3,3-dimethyl-6-morpholinoindoline (85 mg, 0.367 mmol) in DMF (6 mL), 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (100 mg, 367 μmol) and sodium hydride (18 mg, 733 μmol) and heating at 130° C. overnight. After purification 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline was obtained as a yellow film. 1H NMR (500 MHz, chloroform-d) δ ppm 8.73-8.76 (1H, m), 7.80-7.94 (4H, m), 7.40 (1H, ddd, J=7.6, 4.9, 1.5 Hz), 7.20-7.27 (1H, m), 7.08 (1H, d, J=8.3 Hz), 6.31 (1H, dd, J=8.1, 2.2 Hz), 5.59 (1H, d, J=2.4 Hz), 3.69-3.81 (6H, m), 2.89-3.03 (4H, m), 2.37 (3H, s), 1.51 (3H, s), 1.46 (3H, s). Mass Spectrum (ESI) m/e=469 (M+1).

Provenance & Evidence