Sodium Carbonate → HCID 21192478, compound

Participants

Reaction Steps

A mixture of 4,7-dibromoisoquinoline (556 mg, 1.93 mmol), tetrakis(triphenylphosphine)-palladium(0) (73 mg, 3 mol %), phenylboronic acid (238 mg, 1.95 mmol), and aqueous sodium carbonate (Na2CO3) (3.9 mL, 1.0 M, 3.9 mmol) in DME (12 mL) was heated at reflux under nitrogen for 20 h. The mixture was diluted with ethyl acetate (EtOAc) (100 mL), washed with water (30 mL), dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography upon silica gel using hexanes-EtOAc (95:5 to 80:20) as eluant to give 4-bromo-7-phenylisoquinoline (389 mg, 1.37 mmol) as a straw-colour solid; 1H (δ, CDCl3, 300 MHz) 7.4-7.6 (3H, m), 7.65-7.75 (2H, m), 8.1 (1H, d), 8.15 (1H, s), 8.2 (1H, d), 8.7 (1H, s), 9.2 (1H, s); LRMS 283, 284, 286.

Provenance & Evidence