ethyl 2-bromo-3-oxo-3-phenylpropanoate → HCID 66856132、化合物

HRID 1530009ノート

反応式

HRID 1530009 の反応式
[N:1]1[N:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]2=[C:3]([C:10](=[S:12])[NH2:11])[CH:2]=1.Br[CH:14]([C:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C>[N:1]1[N:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]2=[C:3]([C:10]2[S:12][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:11]=2)[CH:2]=1

参加物

4

反応物 2

HCID 237819ethyl 2-bromo-3-oxo-3-phenylpropanoateHCID 46840049Pyrazolo[1,5-a]pyridine-3-carbothioamide

生成物 1

HCID 66856132HCID 66856132、化合物収率 31.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a suspension of commercially available pyrazolo[1,5-a]pyridine-3-carbothioamide (580 mg, 3.3 mmol) in ethanol (20 mL) was added ethyl 2-bromo-3-oxo-3-phenylpropanoate (1.0 g, 3.7 mmol), and the mixture was heated under reflux for 11 hr. The reaction solution was allowed to cool to room temperature, and the resulting solid was collected by filtration and washed with methanol. The collected filtrate and washing solution was concentrated under reduced pressure, and the obtained residue was suspended in ethyl acetate (100 mL). The obtained suspension was washed with saturated aqueous sodium bicarbonate solution (50 mL×2), and the collected aqueous layer was extracted with ethyl acetate (50 mL). The collected organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→100/0) to give the title compound (360 mg, 31%) as a yellow solid.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 11 hr
  3. filtrationthe resulting solid was collected by filtration
  4. washwashed with methanol
  5. washThe collected filtrate and washing solution
  6. concentrationwas concentrated under reduced pressure
  7. washThe obtained suspension was washed with saturated aqueous sodium bicarbonate solution (50 mL×2)
  8. extractionthe collected aqueous layer was extracted with ethyl acetate (50 mL)
  9. dry with materialThe collected organic layer was dried over anhydrous magnesium sulfate
  10. filtrationthe insoluble material was filtered off
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→100/0)

出典と根拠

ORDレコード
ord-7b7efa0cdc994e31bddaea7c7b44a44b
出典データセット
uspto-grants-2015_07
特許番号
US09090601B2

反応ノート

読み込み中…