[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([OH:12])[CH:11]=1)[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2.I[CH:15]([CH3:17])[CH3:16].C([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH:15]([CH3:17])[CH3:16])[CH:11]=1)[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2To 6-fluoro-2-methylquinolin-8-ol (1.0 g, 5.6 mmol) in acetone (20 mL) were added 2-iodopropane (1.9 g, 11 mmol) and K2CO3 (2.3 g, 17 mmol). The reaction was heated to 70° C. for 20 hours in a sealed tube and then cooled. Water was added and the aqueous phase was extracted with DCM. The combined organic phases were washed with brine, dried with MgSO4, filtered and concentrated under reduced pressure to yield 6-fluoro-8-isopropoxy-2-methylquinoline (1.1 g, 89% yield) as a dark oil.
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