Potassium Carbonate → HCID 21966481, compound

Participants

Reaction Steps

A mixture of 6-dimethylamino-3-formyl-1-phenyl boronic acid (11.5 g, 59.5 mmol), 7-bromo-1,4,4,6-tetramethyl-3,4-dihydro-1H-quinoline-2-one (Example 1d) (14.0 g, 49.6 mmol) and potassium carbonate (13.7 g, 99.2 mmol) in toluene (140 mL), ethanol (28 mL) and water (21 mL) was degassed with argon for 40 minutes. Tetrakis(triphenylphosphine)palladium(0) (3.5 g, 0.06 mmol) was added and the mixture heated at reflux under argon for 24 hrs. The solution was cooled to room temperature, diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (30% ethyl acetate in hexane) to give 14.66 g of 4-Dimethylamino-3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-benzaldehyde (84%). 1H NMR (300 MHz; CDCl3): 1.31 (s, 3 H), 1.33 (s, 3 H), 2.10 (s, 3 H), 2.53 (s, 2 H), 2.69 (s, 6 H), 3.36 (s, 3 H), 6.89 (s, 1 H), 6.99 (d, J=8.7 Hz, 1 H), 7.14 (s, 1 H), 7.58 (d, J=2.4 Hz, 1 H), 7.77 (dd, J=2.4 Hz and 8.4 Hz, 1 H), 9.82 (s, 1 H).

Provenance & Evidence