Acetic Anhydride → 1-[2-(Propan-2-yl)pyrazolo[1,5-a]pyridin-3-yl]ethan-1-one

HRID 731745노트

반응식

HRID 731745 반응식
[CH:1]([C:4]1[CH:12]=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].[C:13](OC(=O)C)(=[O:15])[CH3:14]>S(=O)(=O)(O)O>[CH:1]([C:4]1[C:12]([C:13](=[O:15])[CH3:14])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 113786582-Isopropylpyrazolo[1,5-a]pyridine

생성물 1

HCID 159338551-[2-(Propan-2-yl)pyrazolo[1,5-a]pyridin-3-yl]ethan-1-one수율 87%

시약·촉매·용매 1

HCID 1118Sulfuric Acid촉매

실험 절차

2-Isopropyl-pyrazolo[1,5-a]pyridine (10.00 g, 66.7 mmol), acetic anhydride (100 ml), and concentrated sulfuric acid (10 drops) were combined and stirred for 3 hours at reflux. The reaction mixture was cooled to room temperature and poured into ice water (300 ml). The mixture was quenched with 2 N sodium hydroxide until the pH>10, and the quenched solution was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified by silica gel flash chromatography (0 to 40% ethyl acetate in hexanes) to give 11.8 g (87%) of 1-(2-isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-ethanone. 1H-NMR (250 MHz, DMSO-d6) δ 8.47 (d, J=6.8 Hz, 1H), 8.12 (d, J=9.0 Hz, 1H), 7.38 (t, J=7.3 Hz, 1H), 6.89 (t, J=6.0 Hz, 1H), 3.76 (sept, J=6.9 Hz, 1H), 2.60 (s, 3H), 1.39 (d, J=6.8 Hz, 6H); LC/MS 203.3 m/z (M+H+).

후처리

  1. temperatureat reflux
  2. customThe mixture was quenched with 2 N sodium hydroxide until the pH>10
  3. extractionthe quenched solution was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by silica gel flash chromatography (0 to 40% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-0a4f04d9acb64f4fb3bc8f74ff2c6840
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585875B2

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