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Ethyl Acetate → N-(6-(furan-3-yl)-1H-indazol-3-yl)butyramide

HRID 497606
ノート
印刷プレビュー

反応式

HRID 497606 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:19]1[CH:23]=[CH:22][C:21]([C:24]2[CH:32]=[C:31]3[C:27]([C:28]([NH:41][C:42](=[O:46])[CH2:43][CH2:44][CH3:45])=[N:29][N:30]3COCC[Si](C)(C)C)=[CH:26][CH:25]=2)=[CH:20]1.C(OCC)(=O)C>O1CCCC1>[O:19]1[CH:23]=[CH:22][C:21]([C:24]2[CH:32]=[C:31]3[C:27]([C:28]([NH:41][C:42](=[O:46])[CH2:43][CH2:44][CH3:45])=[N:29][NH:30]3)=[CH:26][CH:25]=2)=[CH:20]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 10386231N-[6-(furan-3-yl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide

生成物 1

HCID 9993220N-(6-(furan-3-yl)-1H-indazol-3-yl)butyramide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
66 °C

実験手順

1.95 cm3 of tetrabutylammonium fluoride as a 1M solution in tetrahydrofuran are added to 120 mg of N-[6-(furan-3-yl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide, described previously, in 5 cm3 of tetrahydrofuran. The reaction medium is heated at about 66° C. for 17 hours. The heating is then stopped and 50 cm3 of ethyl acetate are added. This mixture is washed with 50 cm3 of saturated aqueous sodium hydrogen carbonate solution and then with 50 cm3 of saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate, filtered through a sinter funnel and evaporated under reduced pressure (2 kPa; 50° C.). The residue is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 2 cm), eluting with ethyl acetate/cyclohexane (30/70 by volume) and collecting 15 cm3 fractions. The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.). The residue is taken up in 10 cm3 of diisopropyl ether. This solution is filtered through a sinter funnel to give, after drying (90 Pa; 50° C.), 35 mg of N-[6-(furan-3-yl)-1H-indazol-3-yl]butanamide in the form of a white solid melting at 195° C.

後処理

  1. washThis mixture is washed with 50 cm3 of saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered through a sinter funnel
  4. customevaporated under reduced pressure (2 kPa; 50° C.)
  5. customThe residue is purified by chromatography under an argon pressure of 50 kPa
  6. washon a column of silica gel (particle size 40-60 μm; diameter 2 cm), eluting with ethyl acetate/cyclohexane (30/70 by volume)
  7. customcollecting 15 cm3 fractions
  8. additionThe fractions containing the expected product
  9. customevaporated under reduced pressure (2 kPa; 50° C.)
  10. filtrationThis solution is filtered through a sinter funnel
  11. customto give
  12. dry with materialafter drying (90 Pa; 50° C.), 35 mg of N-[6-(furan-3-yl)-1H-indazol-3-yl]butanamide in the form of a white solid melting at 195° C.

出典と根拠

ORDレコード
ord-1f8bd53a1f31463ab9296dea59c4f40f
出典データセット
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06949579B2

反応ノート

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