[F:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:3]=1[NH2:4].Cl.Cl[C:13]1[CH:14]=CC(OC)=[C:17]2[C:22]=1N=C(C)C=C2.COC1C=CC=C2C=1CC[C@H](C)N2.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[F:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:5]2[C:3]=1[N:4]=[C:22]([CH3:17])[CH:13]=[CH:14]28-Fluoro-5-methoxy-2-methylquinoline was synthesized from 2-fluoro-5-methoxyaniline (30.0 g, 213 mmol) according to the procedures described above for 8-chloro-5-methoxy-2-methylquinoline hydrochloride (Intermediate 1, Step 1) with the following change: The hydrochloride salt was dissolved in dichloromethane (400 mL) and the pH of the resulting solution was adjusted to 8-9 with saturated aqueous potassium carbonate solution. The resulting mixture was extracted with dichloromethane, and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 20% ethyl acetate-petroleum ether) to afford 8-fluoro-5-methoxy-2-methylquinoline (25.2 g, 62%) as a yellow solid. MS (ESI, pos. ion) m/z 192 [M+H]+.
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