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

HRID 731745ノート

反応式

HRID 731745 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid触媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-0a4f04d9acb64f4fb3bc8f74ff2c6840
出典データセット
uspto-grants-2009_09
特許番号
US07585875B2

反応ノート

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