Sodium Carbonate → HCID 58695797, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-chloro-2-propionylphenyl trifluoromethanesulfonate (2-5) (21.0 g, 66.3 mmol), absolute ethanol (120 mL), toluene (120 mL), and 2M aqueous solution of sodium carbonate (100 mL) was added ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate (2-3) (20.3 g, 66.3 mmol). The mixture was evacuated and flushed with nitrogen three times. After addition of tetrakis(triphenylphosphine)palladium(0) (7.69 g, 6.63 mmol), the mixture was heated at 75° C. for 1 h and TLC showed no remaining trifluoromethanesulfonate. After cooling to room temperature, the mixture was poured into water and extracted with EtOAc (3×250 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated. Purification of the crude residue by flash chromatography over silica gel (10% ethyl acetate/hexanes as eluent) afforded (2-6) as a colorless oil.

Provenance & Evidence