Br.[F:2][C:3]1[C:4]([CH3:14])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([OH:13])[CH:7]=2.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:22][CH2:23][O:24][CH3:25].O>CN1C(=O)CCC1.C1(C)C=CC=CC=1>[F:2][C:3]1[C:4]([CH3:14])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([O:13][CH2:22][CH2:23][O:24][CH3:25])[CH:7]=2
To a suspension of 3-fluoro-2-methylquinolin-7-ol hydrobromide (0.37 g, 1.43 mmol) and Cs2CO3 (1.08 g, 3.31 mmol) in NMP (6 mL) was added 1-bromo-2-methoxyethane (0.230 g, 1.66 mmol). The reaction mixture was stirred at ambient temperature for 24 hours. Water (10 mL) and toluene (20 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue obtained was purified by flash chromatography on silica gel (2:1 hexane/ethyl acetate) to give 3-fluoro-7-(2-methoxyethoxy)-2-methylquinoline (0.234 g, 0.995 mmol, 90.1% yield).
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