Potassium Carbonate → HCID 60069826, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 7-bromo-1-chloroisoquinoline (3.14 g, 13 mmol) in DMSO (20 mL) at room temperature was added either carboxylic acid tert-butyl (BOC)piperazine (7.23 g, 38.8 mmol) or BOC-homopiperazine (7.77 g, 38.8 mmol) and then potassium carbonate (5.36 g, 39 mmol). The mixture was heated to 110° C. for 24 h. On cooling, the mixture was poured onto ice/water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic phases were washed with water 50 mL) and brine (50 mL). Before drying over anhydrous sodium sulfate. Removal of solvent under reduced pressure gave crude product. Purification was performed by applying the crude material to a plug of silica in a filter funnel and eluting with heptane/ethyl acetate (2:1) and gave 2.73 g (54%) yellow oil. 1H NMR (CDCl3) δ 8.20-8.22 (m, 1H), 8.13-8.18 (d, J=6 Hz, 1H), 7.65-7-71 (dd, J=12, 3 Hz, 1H), 7.59-7.65 (d, J=12 Hz, 1H), 7.21-7.25 (m, 1H), 3.64-3.73 (m, 4H), 7.27-7.36 (m, 4H), 1.49 (s, 9H); LCMS: 392, 394, 395.

Provenance & Evidence