2-Bromoethanol → 4-(4-Chloro-2-fluoroanilino)-7-(2-hydroxyethoxy)-6-methoxyquinoline

HRID 393646Notes

Reaction equation

[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[C:4]([F:22])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][OH:32]>CN(C=O)C.O>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:30][CH2:31][OH:32])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[C:4]([F:22])[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinoline (500 mg, 1.7 mmol), potassium carbonate (232 mg, 1.7 mmol) and 2-bromoethanol (1181l, 1.7 mmol) in DMF (15 ml) was heated at 80° C. for 5 hours. The mixture was allowed to cool, was diluted with water and extracted with ethyl acetate. The combined extracts were washed with water, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (100/0 increasing to 95/5) to give 4-(4-chloro-2-fluoroanilino)-7-(2-hydroxyethoxy)-6-methoxyquinoline (160 mg, 26%).

Workup

temperatureto cool
extractionextracted with ethyl acetate
washThe combined extracts were washed with water
dry with materialdried (MgSO4)
customthe solvent removed by evaporation
customThe residue was purified by column chromatography
washeluting with methylene chloride/methanol (100/0 increasing to 95/5)

Sources & evidence

ORD record: ord-1037030ed0b744bf9937a644ef1b9814
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809097B1

Reaction notes

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