Ethyl Bromide → 7-Ethoxy-6-fluoro-2-methylquinoline

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH3:22]>CC(C)=O>[CH2:21]([O:12][C:11]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][C:7]([CH3:13])=[N:8]2)=[CH:3][C:2]=1[F:1])[CH3:22]

Participants

Procedure

6-fluoro-2-methylquinolin-7-ol (500 mg, 1.41 mmol) (Example 119, Step B), potassium carbonate (585 mg, 4.23 mmol) and bromoethane (308 mg, 2.82 mmol) in acetone (10 mL) were stirred at 70° C. in a sealed tube for 20 hours. After dilution with water (50 mL) the reaction was extracted with DCM. The organic phases were concentrated and the residue 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-ethoxy-6-fluoro-2-methylquinoline (190 mg, 65.6% yield) as a solid.