Cesium carbonate → HCID 50940456, compound

Participants

Reaction Conditions

Reaction Steps

A dry, microwave vial containing 4-(3,3-dimethylindolin-6-yl)morpholine (150.7 mg, 0.65 mmol), 4,8-dichloro-2,3,6-trimethylquinoline (233.8 mg, 0.97 mmol), cesium carbonate (317.0 mg, 0.97 mmol), Pd2(dba)3 (119 mg, 0.13 mmol), rac-BINAP (81.6 mg, 0.13 mmol), and dry 1,4-dioxane (2.2 mL) was evacuated and backfilled with argon. The mixture was heated in the microwave at 140° C. After 2 h, the reaction was filtered then concentrated under reduced pressure. The residue was purified on silica gel (0-100% EtOAc in hexane) to afford an impure film that was triturated with isopropanol to afford 8-chloro-4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-2,3,6-trimethylquinoline. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.71 (1H, d, J=1.5 Hz), 7.52 (1H, s), 7.03 (1H, d, J=8.1 Hz), 6.23 (1H, s), 5.44 (1H, s), 3.72 (1H, d, J=9.0 Hz), 3.59 (4H, m), 3.53 (1H, s), 3.33 (2H, s), 2.83 (4H, s), 2.69 (3H, s), 2.40 (3H, s), 2.18 (3H, s), 1.44 (3H, s), 1.39 (3H, s). Mass Spectrum (ESI) m/e=436.1 (M+1).

Provenance & Evidence