Potassium Carbonate → Methyl 4-(benzyloxy)-7-(4-methoxybenzylamino)isoquinoline-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 4-(benzyloxy)-7-bromoisoquinoline-3-carboxylate (372.0 mg, 1.0 mmol), 4-methoxybenzylamine (0.2 mL, 1.5 mmol, TCI), CuI (19.0 mg, 0.1 mmol), proline (23.0 mg, 0.2 mmol) and K2CO3 (276.4 mg, 2.0 mmol) in DMSO (0.6 mL) was stirred at 80° C. for 24 hours under a nitrogen atmosphere. After cooling to room temperature, the mixture was diluted with CH2Cl2 (50 mL) and H2O (50 mL). The layers were separated and the aqueous layer was extracted twice with CH2Cl2. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-30% EtOAc/CH2Cl2) to give the title compound in 137.0 mg. 1H NMR (CDCl3, 200 MHz): δ=8.82 (s, 1H), 7.96 (d, 1H, J=9.0 Hz), 7.54 (d, 2H, J=6.6 Hz), 7.42-7.27 (m, 5H), 7.05 (d, 1H, J=9.0 Hz), 6.93-6.87 (m, 3H), 5.18 (s, 2H), 4.38 (d, 2H, J=5.0 Hz), 4.00 (s, 3H), 3.82 (s, 3H).

Provenance & Evidence