Sodium Carbonate → HCID 117680428, compound

Participants

Reaction Conditions

Reaction Steps

(R)-quinuclidin-3-yl((3-(4-bromophenethoxy)phenyl)(phenyl)methyl)carbamate (0.40 g, 0.747 mmol), 4-formylphenylboronic acid (0.123 g, 0.822 mmol), and sodium carbonate (0.158 g, 1.494 mmol) were combined in toluene (9.94 mL) and water (2.48 mL). The mixture was degassed with nitrogen for 10 minutes. Tetrakis-(triphenylphosphine)palladium(0) (0.087 g, 0.075 mmol) was added, and the mixture heated at 120° C. for 30 minutes in a microwave. The mixture was filtered, and the filtrate partitioned between ethyl acetate and water. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to afford a brown oil. The crude material was partially purified using a flash C18 cartridge eluting with 30-60% acetonitrile in water to afford a brown oil (0.174 g). The material was used directly in the next step with no further purification.

Provenance & Evidence