Pyridine → (3-Bromo-7-fluoro-quinolin-6-yl)-acetic acid methyl ester

HRID 655252ノート

反応式

HRID 655252 の反応式
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[F:15])[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[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[F:15])[N:11]=[CH:10][C:9]([Br:23])=[CH:8]2

参加物

5

反応物 3

HCID 1049PyridineHCID 24408BromineHCID 59320292(7-Fluoro-quinolin-6-yl)-acetic acid methyl ester

生成物 1

HCID 68706227(3-Bromo-7-fluoro-quinolin-6-yl)-acetic acid methyl ester収率 75%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

To a mixture of (7-fluoro-quinolin-6-yl)-acetic acid methyl ester (14.0 g, 63.9 mmol) and pyridine (10.4 mL, 127.8 mmol) in 200 mL of carbon tetrachloride was added bromine (6.6 mL, 127.8 mmol) in a dropwise fashion. The mixture was heated to reflux for 2 hrs before being cooled to ambient temperature. The liquid in the flask was decanted and washed with NaHCO3 and water. The dark solid on the bottom of the flask was treated with NaHCO3 and dichloromethane. The combined organic layers were washed with water, dried (Na2SO4) and evaporated to dryness. The crude product was purified via flash column chromatography eluting with petroleum ether/ethyl acetate (40/1˜3/1) to return 13.9 g (75% yield) of the title compound as white crystalline solid. 1H NMR (DMSO-d6): δ 8.89 (s, 1H), 8.27 (m, 1H), 7.66˜7.74 (m, 2H), 3.87 (s, 2H), 3.74 (s, 3H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hrs
  3. customThe liquid in the flask was decanted
  4. washwashed with NaHCO3 and water
  5. additionThe dark solid on the bottom of the flask was treated with NaHCO3 and dichloromethane
  6. washThe combined organic layers were washed with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated to dryness
  9. customThe crude product was purified via flash column chromatography
  10. washeluting with petroleum ether/ethyl acetate (40/1˜3/1)

出典と根拠

ORDレコード
ord-678e4e7d32e841f6a4430c1f3bc5960d
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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