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

HRID 896766

반응식

HRID 896766 반응식
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[CH:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[C:18](OC(=O)C)(=[O:20])[CH3:19].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]([F:17])=[CH:13][CH:12]=3)[C:10]([C:18](=[O:20])[CH3:19])=[C:6]2[CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 6356Boron trifluorideHCID 7918Acetic AnhydrideHCID 111841947-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine

생성물 1

HCID 223500461-(7-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl)ethanone수율 77%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine (10.0 g, 40.5 mmol) in toluene (225 mL) at room temperature was added acetic anhydride (4.6 mL, 48.6 mmol). Boron trifluoride diethyletherate (5.6 mL, 44.6 mmol) was then added dropwise and the resultant solution was heated to reflux for 3.5 hours. The reaction mixture was cooled to room temperature and quenched by the dropwise addition of aqueous sodium bicarbonate. Ether was added and the organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics were dried over magnesium sulfate, filtered and concentrated. The residue was purified by recrystallization from ethyl acetate-hexanes to give 1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone (9.0 g, 77%) as redish needles. 1H NMR (CDCl3): δ 8.41 (d, 1 H), 7.59 (m, 2 H), 7.45 (dd, 1 H), 7.26-7.13 (m 3 H), 2.15 (s, 3 H); 19F NMR (CDCl3) δ −112.06; MS m/289 (M+1).

후처리

  1. temperatureto reflux for 3.5 hours
  2. customquenched by the dropwise addition of aqueous sodium bicarbonate
  3. additionEther was added
  4. washthe organic layer was washed with brine
  5. extractionThe aqueous layer was extracted with ether
  6. dry with materialthe combined organics were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by recrystallization from ethyl acetate-hexanes

출처 및 근거

ORD 기록
ord-42d9002008bc4fb88124923bfafc7c1e
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919352B2

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