Sodium Carbonate → 4-(3-Cyanophenyl)-1-methoxyisoquinoline

Participants

Reaction Steps

A stirred mixture of 4-bromo-1-methoxyisoquinoline (1.19 g, 4.72 mmol), 3-cyanophenylboronic acid (1.04 g, 7.08 mmol), palladium tetrakis(triphenylphosphine) (0.33 g. 0.28 mmol), 2 m aq sodium carbonate (4.72 mmol) and toluene (30 mL) is heated 42 hr at reflux under a nitrogen atmosphere. After cooling, the solvent is removed and the residue is purified by chromatography eluting with cyclohexane-2.5 to 6% ethyl acetate. Product containing fractions are combined and concentrated to afford 4-(3-cyanophenyl)-1-methoxyisoquinoline (200 mg, 15.5% yield). LC/MS: MS m/e=275 (M+H); RT 4.38; 1H NMR (δ ppm): 8.22 (1H, d), 7.98 (1H, d), 7.83 (1H, s); 7.78 (1H, t), 7.65 (2H, m), 7.58 (1H, t), 7.18 (1H, d); 4.11 (3H, s), 2.23 (3H, s).

Provenance & Evidence