Tetrahydrofuran → 7-Benzyl-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

Participants

Reaction Steps

To a mixture of 4-benzyloxy-7-bromo-isoquinoline-3-carboxylic acid methyl ester (150 mg, 0.40 mmol), Pd(PPh3)4 (47 mg, 0.040 mmol) and THF (4 mL) was added benzylzinc bromide (2 mL, 1.0 mmol, 0.5 M in THF), and the resulting mixture was refluxed for 16 h under nitrogen atmosphere. After cooling the mixture to r.t., saturated NH4Cl (50 mL) and CH2Cl2 (50 mL) were added. The aqueous layer was extracted with additional CH2Cl2, and the organic layers were combined and dried over MgSO4. After evaporating the solvent, the crude product was purified by column chromatography (0-35% EtOAc/hexanes) to give 19 mg of the title compound as a yellow solid. MS: (+) m/z 294.05 (M+1).

Provenance & Evidence