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

HRID 655272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655272
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6c49c685523e4e138d3528287c45c729
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071581B2

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