Boron trifluoride → 1-[5-(Chloro)-2-(4-methoxyphenyl) pyrazolo[1,5-alpha]pyridin-3-yl]ethanone

HRID 724001ノート

反応式

HRID 724001 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[CH:10]=[C:4]2[CH:3]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20].B(F)(F)F>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)[C:10]([C:19](=[O:21])[CH3:20])=[C:4]2[CH:3]=1

参加物

5

反応物 3

HCID 6356Boron trifluorideHCID 7918Acetic AnhydrideHCID 221809255-Chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridine

生成物 1

HCID 693562251-[5-(Chloro)-2-(4-methoxyphenyl) pyrazolo[1,5-alpha]pyridin-3-yl]ethanone収率 66.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 5-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridine (3.0 g, 11.6 mmol) in toluene (100 mL) at room temperature was added acetic anhydride (1.6 mL, 17.4 mmol). Boron trifluoride diethyletherate (1.8 mL, 13.9 mmol) was then added dropwise and the resulting solution was heated at reflux for 4 hours. The reaction mixture was cooled to room temperature and quenched by the dropwise addition of saturated aqueous sodium bicarbonate. The reaction was extracted with ethyl acetate, and the ethyl acetate phase washed with brine, dried (magnesium sulfate), filtered and concentrated. The residue was purified by recrystallization from ethyl acetate-hexanes to give 1-[5-(chloro)-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-3-yl]ethanone (2.31 g, 66%). 1H NMR (CDCl3): δ 8.44 (d, 1H), 8.40 (d, 1H), 7.49 (d, 2H), 7.02 (d, 2H), 6.97 (dd, 1H), 3.85 (s, 3H), 2.15 (s, 3H); MS m/z 301 (M+1).

後処理

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for 4 hours
  3. customquenched by the dropwise addition of saturated aqueous sodium bicarbonate
  4. extractionThe reaction was extracted with ethyl acetate
  5. washthe ethyl acetate phase washed with brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by recrystallization from ethyl acetate-hexanes

出典と根拠

ORDレコード
ord-1e815a14184b485f8751bb5f3282dd61
出典データセット
uspto-grants-2006_11
特許番号
US07141569B2

反応ノート

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