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

HRID 655272ノート

反応式

HRID 655272 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6c49c685523e4e138d3528287c45c729
出典データセット
uspto-grants-2011_12
特許番号
US08071581B2

反応ノート

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