ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Ethyl Acetate → N-(5-bromo-6-chloro-1H-indazol-3-yl)butanamide

HRID 497645
ノート
印刷プレビュー

反応式

HRID 497645 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Br:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][C:28]=1[Cl:29])[N:25](COCC[Si](C)(C)C)[N:24]=[C:23]2[NH:38][C:39](=[O:43])[CH2:40][CH2:41][CH3:42].C(OCC)(=O)C>O1CCCC1>[Br:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][C:28]=1[Cl:29])[NH:25][N:24]=[C:23]2[NH:38][C:39](=[O:43])[CH2:40][CH2:41][CH3:42]
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 22319528N-[5-bromo-6-chloro-1-[(2-trimethylsilylethoxy)methyl]indazol-3-yl]butanamide

生成物 1

HCID 10087157N-(5-bromo-6-chloro-1H-indazol-3-yl)butanamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
67 °C

実験手順

12.6 cm3 of tetrabutylammonium fluoride as a 1M solution in tetrahydrofuran are added to 940 mg of N-[5-bromo-6-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide, described previously, in 30 cm3 of tetrahydrofuran. The medium is then maintained at 67° C. for 19 hours and is then allowed to return to room temperature and 50 cm3 of ethyl acetate are added. The organic phase is washed with 2×50 cm3 of saturated aqueous sodium hydrogen carbonate solution and then with 50 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2 kPa; 45° 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 3.5 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.) and the residue is taken up in 15 cm3 of diisopropyl ether, filtered off on a sinter funnel and washed successively with 5 cm3 of ethyl acetate and then with 2×10 cm3 of diisopropyl ether. After drying (90 Pa; 50° C.), 460 mg of N-(5-bromo-6-chloro-1H-indazol-3-yl)butanamide are obtained in the form of a white solid melting at 250° C.

後処理

  1. customto return to room temperature
  2. washThe organic phase is washed with 2×50 cm3 of saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialwith 50 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2 kPa; 45° C.)
  6. customThe residue is purified by chromatography under an argon pressure of 50-kPa
  7. washon a column of silica gel (particle size 40-60 μm; diameter 3.5 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume)
  8. additionThe fractions containing the expected product
  9. customevaporated under reduced pressure (2 kPa; 50° C.)
  10. filtrationfiltered off on a sinter funnel
  11. washwashed successively with 5 cm3 of ethyl acetate
  12. dry with materialAfter drying (90 Pa; 50° C.), 460 mg of N-(5-bromo-6-chloro-1H-indazol-3-yl)butanamide

出典と根拠

ORDレコード
ord-ab4dfbb49d7143c1aafc38c3b77e9bb7
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

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート