Potassium Carbonate → 8-Fluoro-7-(2-methoxyethoxy)-2-methylquinoline

HRID 339002Notes

Reaction equation

[F:1][C:2]1[C:3]([OH:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][O:23][CH3:24]>CC(C)=O>[F:1][C:2]1[C:3]([O:13][CH2:21][CH2:22][O:23][CH3:24])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of 8-fluoro-2-methylquinolin-7-ol (0.30 g, 1.69 mmol) and potassium carbonate (0.70 mg, 5.08 mmol) in acetone (7 mL) was added 1-bromo-2-methoxyethane (0.47 g, 3.39 mmol) and the mixture heated at 70° C. for 18 hours. Additional bromo-2-methoxyethane (0.150 mL) and potassium carbonate (0.35 g) were added and heating was continued for 16 hours. The mixture was partitioned between water and ethyl acetate and the layers were separated. The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Biotage, 25M; 25% ethyl acetate:hexanes) to afford 8-fluoro-7-(2-methoxyethoxy)-2-methylquinoline (0.217 g, 54%).

Workup

temperatureheating
customThe mixture was partitioned between water and ethyl acetate
customthe layers were separated
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography (Biotage, 25M; 25% ethyl acetate:hexanes)

Sources & evidence

ORD record: ord-be6da6fc5ee34d0b8a65eb10491e6dd4
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889704B2

Reaction notes

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