Sodium Carbonate → HCID 18507795, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-adamantan-1-ylmethyl-6-bromo-1,3-dihydro-indol-2-one (1.85 g, 5.13 mmol) in toluene (23 ml) and ethanol (21 ml) were added tetrakis(triphenylphosphine)palladium (0.60 g, 0.513 mmol), sodium carbonate (1.09 g, 10.27 mmol) in water (11 ml) and solid 4-cyanophenylboronic acid (1.51 g, 10.27 mmol). The mixture was heated at 100° C. overnight. The reaction mixture was partitioned between chloroform and aqueous saturated potassium carbonate (50 ml). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under vacuum to give the crude product. This was chromatographed on flash silica gel eluting with a 15% ethyl acetate in hexane to give the title compound of 9C as a white solid (0.594 g, 30.3% yield).

Provenance & Evidence