Triethylamine → HCID 86648161, compound

Participants

Reaction Conditions

Reaction Steps

In a 20 mL microwave tube was charged cesium carbonate (0.440 mL, 5.50 mmol), palladium(II)acetate (0.018 g, 0.079 mmol), and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.068 g, 0.118 mmol) in dioxane (6.0 mL) to give a yellow suspension. The mixture was stirred for 10 minutes and then triethylamine (0.016 mL, 0.118 mmol) was added. The solution was stirred for another 10 minutes; and then 6-bromo-2-phenylquinoline (1.1168 g, 3.93 mmol) and benzophenone imine (0.791 mL, 4.72 mmol) were added as a solution in dioxane (6.0 mL). The mixture was heated at 100° C. overnight. The mixture was cooled to room temperature and dilute with ethyl acetate. The organics were washed 2×100 mL with water, dried over magnesium sulfate, filtered, and concentrated onto silica gel. The reaction was purified by flash chromatography using an Argonaut Flashmaster Solo, 20 g column (10% ethyl acetate:hexanes for 30 min) to afford a yellow oil. (ESI(+)) m/e 385.0 (M+H)+.

Provenance & Evidence