Sodium Carbonate → HCID 87782654, compound

Participants

Reaction Steps

To a stirred solution of 5-bromoindan-1-one oxime (0.25 g, 1.10 mmol) in glyme (11 mL) was added 3-cyanophenyl boronic acid (0.21 g, 1.44 mmol), sodium carbonate (0.35 g, 3.30 mmol) dissolved in deionized (D.I.) water (2 mL), and tetrakis(triphenylphosphine) palladium (0) (0.06 g, 0.05 mmol). The resulting solution was heated to reflux for 2 hours. The solution was cooled to room temperature and partitioned between ammonium chloride solution (sat.) and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was purified on a silica gel column (20% ethyl acetate/hexane) and triturated with ether to give 3-[(1E)-1-(hydroxyimino)-2,3-dihydro-1H-inden-5-yl]benzonitrile as a white solid (0.12 g, 43%). MS (ESI) m/z 249; HRMS: calcd for C16H12N2O+H+, 249.10224; found (ESI, [M+H]+), 249.1033.

Provenance & Evidence