Sodium hydride → 4-(3,3-Dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-8-fluoro-3-methyl-2-(2-pyridinyl)quinoline

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Reaction Conditions

Reaction Steps

Prepared according to procedure M using 4-chloro-8-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (235 mg, 0.86 mmol), 4-(3,3-dimethylindolin-6-yl)morpholine (200 mg, 0.86 mmol), sodium hydride (41 mg, 1.72 mmol) in DMF (2.0 mL) and heating at 130° C. for 4 h. After purification 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-8-fluoro-3-methyl-2-(2-pyridinyl)quinoline was obtained as a yellow film. 1H NMR (400 MHz, chloroform-d) δ ppm 8.64-8.79 (1H, m), 7.87-7.98 (2H, m), 7.60-7.65 (1H, m), 7.32-7.42 (3H, m), 7.08 (1H, d, J=7.8 Hz), 6.31 (1H, dd, J=8.0, 2.2 Hz), 5.59 (1H, d, J=2.3 Hz), 3.63-3.83 (6H, m), 2.86-3.05 (4H, m), 2.43 (3H, s), 1.52 (3H, s), 1.47 (3H, s). Mass Spectrum (ESI) m/e=469 (M+1).

Provenance & Evidence