Boron trifluoride → 1-[7-(Chloro)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone

HRID 896776

反応式

HRID 896776 の反応式
[Cl:1][C:2]1[N:7]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:6]2[CH:5]=[CH:4][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[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[C:10]([C:19](=[O:21])[CH3:20])=[C:6]2[CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6356Boron trifluorideHCID 7918Acetic AnhydrideHCID 223500457-Chloro-2-(4-methoxyphenyl)pyrazolo[1,5-A]pyridine

生成物 1

HCID 223500511-[7-(Chloro)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone収率 65.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridine (18.7 g, 72.4 mmol) in toluene (300 mL) at room temperature was added acetic anhydride (8.2 mL, 86.9 mmol). Boron trifluoride diethyletherate (10.1 mL, 79.6 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-[7-(chloro)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone (14.2 g, 65%) as reddish needles. 1H NMR (CDCl3): δ 8.37 (dd, 1H), 7.49 (dd, 2H), 7.39 (dd, 1H), 7.10 (dd, 1H), 6.98 (dd, 2H), 3.84 (s, 3H), 2.13 (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-78094efd05224ce8924d1fe3f3a74fe2
出典データセット
uspto-grants-2005_07
特許番号
US06919352B2

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