Morpholine → 4-(3,3-Dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-7-fluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline

Participants

Reaction Conditions

Reaction Steps

Prepared according to procedure N using 7-fluoro-4-(6-iodo-3,3-dimethylindolin-1-yl)-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline (68 mg, 0.12 mmol) (described herein), morpholine (20 μL, 0.23 mmol), Pd2dba3 (7.4 mg, 8.1 μmol), 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (8.2 mg, 0.017 mmol), and sodium tert-butoxide (22.1 mg, 0.23 mmol) in toluene (2.2 mL), and heated at 95° C. for 15 h. After purification 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-7-fluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline was obtained as a yellow glass. 1H NMR (400 MHz, chloroform-d) δ ppm 8.17-8.28 (1H, m), 7.94 and 8.08 (1H, m), 7.74-7.84 (1H, m), 7.63-7.74 (2H, m), 7.42-7.53 (1H, m), 7.29-7.40 (1H, m), 6.98-7.13 (1H, m), 6.21-6.39 (1H, m), 5.65 and 5.82 (1H, m), 3.94 and 3.66 (1H, m), 3.69-3.82 (5H, m), 3.15 (1H, m), 3.05-3.12 (3H, m), 2.84-3.05 (4H, m), 1.94 (2H, s), 1.47-1.55 (3H, m), 1.40-1.47 (3H, m). Mass Spectrum (ESI) m/e=546 (M+1).

Provenance & Evidence