Br[CH2:2][CH2:3][O:4][CH3:5].[CH3:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[C:10]([CH3:18])[C:11]([OH:17])=[CH:12][CH:13]=2)[N:8]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH3:5][O:4][CH2:3][CH2:2][O:17][C:11]1[C:10]([CH3:18])=[C:9]2[C:14]([CH:15]=[CH:16][C:7]([CH3:6])=[N:8]2)=[CH:13][CH:12]=1
1-Bromo-2-methoxyethane (0.64 g, 4.6 mmol), 2,8-dimethylquinolin-7-ol (1.0 g, 2.3 mmol) and potassium carbonate (0.96 g, 6.9 mmol) in acetone (15 mL) were heated to 70° C. in a sealed tube for 18 hours. After cooling, water (20 mL) was added and the aqueous phase was extracted with DCM. The combined organic phases were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography (SP4, 25M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 7-(2-methoxyethoxy)-2,8-dimethylquinoline (90 mg, 17% yield) as an oil
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