Cesium carbonate → 4-(3,3-Dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-2-(2-fluorophenyl)-3-methylquinoline

Participants

Reaction Steps

Prepared according to procedure T using 4-(3,3-dimethylindolin-6-yl)morpholine (0.043 g, 0.184 mmol), 4-chloro-2-(2-fluorophenyl)-3-methylquinoline (0.050 g, 0.184 mmol), cesium carbonate (0.12 g, 0.368 mmol), Pd2(dba)3 (0.017 g, 0.018 mmol) and (±) BINAP (0.0174 g, 0.028 mmol) in 1,4-dioxane (1 mL). After purification by HPLC 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-2-(2-fluorophenyl)-3-methylquinoline was obtained. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.00 (1H, d, J=7.8 Hz), 7.82 (1H, d, J=8.2 Hz), 7.69 (1H, t, J=7.6 Hz), 7.52 (3H, m), 7.30 (2H, m), 6.98 (1H, d, J=8.2 Hz), 6.20 (1H, dd, J=8.2, 2.0 Hz), 5.46 (1H, d, J=2.0 Hz), 3.75 (1H, d, J=9.0 Hz), 3.60 (1H, d, J=9.4 Hz), 3.51 (4H, m), 2.77 (4H, m), 1.99 (3H, s), 1.39 (3H, s), 1.30 (3H, s). Mass Spectrum (ESI) m/e=468 (M+1).

Provenance & Evidence