Morpholine → 6-bromo-N-(4-methoxybenzyl)-3-morpholinoquinolin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-3-iodo-N-(4-methoxybenzyl)quinolin-2-amine (710 mg, 1.5 mmol), morpholine (1.9 mL, 22.7 mmol), Cu(I)(14.4 mg, 0.08 mmol), cesium carbonate (986 mg, 3.0 mmol), 2-isobutyrylcyclohexanone (50.9 mg, 0.30 mmol) and DMF (10 mL) was heated to 125° C. in a microwave unit for 20 min. The mixture was concentrated in vacuo then partioned the crude product between EtOAc and water. The organic layer was washed with water and brine 3× each, dried over MgSO4 and concentrated in vacuo to give an orange colored oil. This material was purified by silica flash chromatography (0-5% MeOH/DCM) to give 6-bromo-N-(4-methoxybenzyl)-3-morpholinoquinolin-2-amine as a yellow colored oil.

Provenance & Evidence