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

HRID 861105

반응식

HRID 861105 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-62a819332458421c8759b30165ad8d56
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153855B2

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