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Tetrabutylammonium Fluoride → N-[6-chloro-5-(4-pyridyl)-1H-indazol-3-yl]butanamide

HRID 497660
ノート
印刷プレビュー

反応式

HRID 497660 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:28]=[C:27]2[C:23]([C:24]([NH:37][C:38](=[O:42])[CH2:39][CH2:40][CH3:41])=[N:25][N:26]2COCC[Si](C)(C)C)=[CH:22][C:21]=1[C:43]1[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=1>O1CCCC1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[Cl:19][C:20]1[CH:28]=[C:27]2[C:23]([C:24]([NH:37][C:38](=[O:42])[CH2:39][CH2:40][CH3:41])=[N:25][NH:26]2)=[CH:22][C:21]=1[C:43]1[CH:44]=[CH:45][N:46]=[CH:47][CH:48]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 22319682N-[6-chloro-5-(4-pyridyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide

生成物 1

HCID 22319680N-[6-chloro-5-(4-pyridyl)-1H-indazol-3-yl]butanamide収率 58.8%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate
溶媒
HCID 516892Sodium Bicarbonate溶媒

実験手順

10.4 cm3 of tetrabutylammonium fluoride as a 1M solution in tetrahydrofuran are added to 770 mg of N-[6-chloro-5-(4-pyridyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide, described previously, in 30 cm3 of tetrahydrofuran, and the mixture is refluxed for 18 hours. The reaction medium is diluted with 75 cm3 of ethyl acetate and 75 cm3 of saturated sodium hydrogen carbonate solution. The organic phase is separated out after settling of the phases has taken place, washed with 50 cm3 of saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated to dryness 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 ethyl acetate. The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.); the residue is taken up in 20 cm3 of ethyl acetate, filtered off, washed with 5 cm3 of ethyl acetate and 20 cm3 diethyl ether, and dried under reduced pressure (90 Pa; 45° C.) to give 320 mg of N-[6-chloro-5-(4-pyridyl)-1H-indazol-3-yl]butanamide in the form of white crystals melting above 260° C.

後処理

  1. temperaturethe mixture is refluxed for 18 hours
  2. customThe organic phase is separated out
  3. washwashed with 50 cm3 of saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness 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 ethyl acetate
  10. additionThe fractions containing the expected product
  11. customevaporated under reduced pressure (2 kPa; 50° C.)
  12. filtrationfiltered off
  13. washwashed with 5 cm3 of ethyl acetate and 20 cm3 diethyl ether
  14. customdried under reduced pressure (90 Pa; 45° C.)

出典と根拠

ORDレコード
ord-ae7e4150d8204836a4ce8baa72b9bfa6
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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