Hydroxyamine hydrochloride → 1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone oxime

HRID 2409040ノート

反応式

HRID 2409040 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[N:13]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:12]=[CH:11][C:5]2=[N:6][C:7]=1[C:8](=O)[CH3:9].CC([O-])=O.[Na+].Cl.[NH2:30][OH:31]>CCO>[F:1][C:2]1[CH:3]=[C:4]2[N:13]([S:14]([C:17]3[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:12]=[CH:11][C:5]2=[N:6][C:7]=1[C:8](=[N:30][OH:31])[CH3:9]

参加物

5

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866898561-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone

生成物 1

HCID 1364091011-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone oxime収率 90%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

A mixture of 1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone (0.7 g, 2.118 mmol), NaOAc (1.73 g, 21.1 mmol), and hydroxylamine hydrochloride (0.735 g, 10.55 mmol) in EtOH (20 mL) was heated at 60° C. for 1 h. The reaction mixture was concentrated under reduced pressure, water (200 mL) was added, and the mixture was extracted with EtOAc (50 mL×3). The combined extracts were concentrated under reduced pressure to afford 0.66 mg (90%) of 1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone oxime as a white solid. MS (ESI): m/z=348.2 [M+1]+.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water (200 mL)
  2. additionwas added
  3. extractionthe mixture was extracted with EtOAc (50 mL×3)
  4. concentrationThe combined extracts were concentrated under reduced pressure

出典と根拠

ORDレコード
ord-80b21df78f78489e9794a8fa51ef71fa
出典データセット
uspto-grants-2014_08
特許番号
US08815877B2

反応ノート

読み込み中…