Cesium carbonate → 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-2,3,8-trimethylquinoline

Participants

Reaction Steps

Prepared according to procedure T using 4-(3,3-dimethylindolin-6-yl)morpholine (0.151 g, 0.65 mmol), 4-chloro-2,3,8-trimethylquinoline (0.267 g, 1.3 mmol), cesium carbonate (0.424 g, 1.3 mmol), Pd2(dba)3 (0.060 g, 0.065 mmol) and (±) BINAP (0.061 g, 0.098 mmol) were added together in 1,4-dioxane (2 mL). Crude residue was purified via HPLC to give 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-2,3,8-trimethylquinoline. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.40 (1H, d, J=7.8 Hz), 7.34 (1H, d, J=7.0 Hz), 7.17 (1H, m), 6.85 (1H, d, J=8.2 Hz), 6.04 (1H, dd, J=8.0, 2.2 Hz), 5.20 (1H, d, J=2.3 Hz), 3.50 (1H, d, J=9.0 Hz), 3.39 (5H, m), 2.63 (4H, dd, J=5.9, 3.9 Hz), 2.54 (3H, s), 2.52 (3H, s), 2.04 (3H, s), 1.26 (3H, s), 1.21 (3H, s). Mass Spectrum (ESI) m/e=407 (M+1).

Provenance & Evidence