Tetrabutylammonium Fluoride → N-[6-[3-(phenylmethoxy)phenyl]-1H-indazol-3-yl]butanamide

HRID 497657ノート

反応式

HRID 497657 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]1([CH2:25][O:26][C:27]2[CH:28]=[C:29]([C:33]3[CH:41]=[C:40]4[C:36]([C:37]([NH:50][C:51](=[O:55])[CH2:52][CH2:53][CH3:54])=[N:38][N:39]4COCC[Si](C)(C)C)=[CH:35][CH:34]=3)[CH:30]=[CH:31][CH:32]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCCC1.C(OCC)(=O)C>[C:19]1([CH2:25][O:26][C:27]2[CH:28]=[C:29]([C:33]3[CH:41]=[C:40]4[C:36]([C:37]([NH:50][C:51](=[O:55])[CH2:52][CH2:53][CH3:54])=[N:38][NH:39]4)=[CH:35][CH:34]=3)[CH:30]=[CH:31][CH:32]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

5

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 22319536N-[6-[3-(phenylmethoxy)phenyl]-1-[[2-(trimethylsilyl)ethoxy]-methyl]-1H-indazol-3-yl]butanamide

生成物 1

HCID 22319688N-[6-[3-(phenylmethoxy)phenyl]-1H-indazol-3-yl]butanamide収率 57.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

2.9 cm3 of tetrabutylammonium fluoride as a 1M solution in tetrahydrofuran are added to 1 g of N-[6-[3-(phenylmethoxy)phenyl]-1-[[2-(trimethylsilyl)ethoxy]-methyl]-1H-indazol-3-yl]butanamide, described previously, in 20 cm3 of tetrahydrofuran, and the mixture is refluxed for 18 hours. The reaction medium is diluted with 100 cm3 of ethyl acetate and the organic phase is washed successively with 50 cm3 of saturated sodium hydrogen carbonate solution, with 2×50 cm3 of water and with 50 cm3 of saturated sodium chloride solution. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulphate, filtered and concentrated under reduced pressure (2 kPa; 50° C.). The crude product obtained is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with a cyclohexane/ethyl acetate gradient (70/30 to 40/60 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.); 0.43 g of N-[6-[3-(phenylmethoxy)phenyl]-1H-indazol-3-yl]butanamide is obtained in the form of a white powder.

後処理

  1. temperaturethe mixture is refluxed for 18 hours
  2. washthe organic phase is washed successively with 50 cm3 of saturated sodium hydrogen carbonate solution, with 2×50 cm3 of water and with 50 cm3 of saturated sodium chloride solution
  3. customThe organic phase is separated out
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure (2 kPa; 50° C.)
  7. customThe crude product obtained
  8. customis purified by chromatography under an argon pressure of 50 kPa
  9. washon a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with a cyclohexane/ethyl acetate gradient (70/30 to 40/60 by volume)
  10. additionThe fractions containing the expected product
  11. customevaporated under reduced pressure (2 kPa; 50° C.)

出典と根拠

ORDレコード
ord-87c332f43d4b42afa6de632aedc53f92
出典データセット
uspto-grants-2005_09
特許番号
US06949579B2

反応ノート

読み込み中…