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

HRID 655272노트

반응식

HRID 655272 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6c49c685523e4e138d3528287c45c729
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071581B2

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