Cesium carbonate → (R)-6-fluoro-7-(2-methoxypropoxy)-2-methylquinoline

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 6-fluoro-2-methylquinolin-7-ol (0.200 g, 1.13 mmol), Cs2CO3 (0.552 g, 1.69 mmol) and NMP (2.3 mL) was added (R)-2-methoxypropyl 4-methylbenzenesulfonate (0.303 g, 1.24 mmol). The reaction mixture was heated at 80° C. for 1 hour. After cooling, the reaction was partitioned between toluene and water. The aqueous layer was extracted with toluene (2×). The combined organic layers were washed with water and brine, dried and concentrated. The residue was purified by flash chromatography on silica gel (hexanes:EtOAc, 1:1) to give (R)-6-fluoro-7-(2-methoxypropoxy)-2-methylquinoline (0.289 g, 103%).

Provenance & Evidence