Pyridine → Methyl 2-(3-bromo-5-fluoroquinolin-6-yl)acetate

HRID 655272Notes

Reaction equation

HRID 655272 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:6]([F:15])=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2.N1C=CC=CC=1.[Br:23]Br>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:6]([F:15])=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9]([Br:23])=[CH:8]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 24408BromineHCID 68534543(5-Fluoro-quinolin-6-yl)-acetic acid methyl ester

Product 1

HCID 68534587Methyl 2-(3-bromo-5-fluoroquinolin-6-yl)acetate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of (5-fluoro-quinolin-6-yl)-acetic acid methyl ester (2.0 g, 9 mmol) in CCl4 (20 ml) and pyridine (1.48 ml, 18 mmol) was added bromine (0.9 ml, 18 mmol) dropwise at 5° C. The solution was heated to reflux for 20 minutes. After cooling, the reaction was quenched by sat. aq. NaHCO3 and the mixture extracted with dichloromethane and concentrated. The residue was purified by flash column chromatography to return the title compound (1.8 g, 66%). 1H-NMR (CDCl3, 300 MHz): 8.9 (d, 1H), 8.5 (d, 1H), 7.8 (d, 1H), 7.6 (m, 1H), 3.9 (d, 2H), 3.7 (s, 3H).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 20 minutes
  3. temperatureAfter cooling
  4. customthe reaction was quenched by sat. aq. NaHCO3
  5. extractionthe mixture extracted with dichloromethane
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-6c49c685523e4e138d3528287c45c729
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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