Water → 3-Fluoro-7-(2-methoxyethoxy)-2-methylquinoline

HRID 339095Notes

Reaction equation

HRID 339095 reaction equation
Br.[F:2][C:3]1[C:4]([CH3:14])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([OH:13])[CH:7]=2.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:22][CH2:23][O:24][CH3:25].O>CN1C(=O)CCC1.C1(C)C=CC=CC=1>[F:2][C:3]1[C:4]([CH3:14])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([O:13][CH2:22][CH2:23][O:24][CH3:25])[CH:7]=2

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 1363380793-Fluoro-2-methylquinolin-7-ol hydrobromide

Product 1

HCID 709835103-Fluoro-7-(2-methoxyethoxy)-2-methylquinolineYield 90.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a suspension of 3-fluoro-2-methylquinolin-7-ol hydrobromide (0.37 g, 1.43 mmol) and Cs2CO3 (1.08 g, 3.31 mmol) in NMP (6 mL) was added 1-bromo-2-methoxyethane (0.230 g, 1.66 mmol). The reaction mixture was stirred at ambient temperature for 24 hours. Water (10 mL) and toluene (20 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue obtained was purified by flash chromatography on silica gel (2:1 hexane/ethyl acetate) to give 3-fluoro-7-(2-methoxyethoxy)-2-methylquinoline (0.234 g, 0.995 mmol, 90.1% yield).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by flash chromatography on silica gel (2:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0b1c6b0fec774b23a31f7a650ff2f81e
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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