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

HRID 2409033노트

반응식

HRID 2409033 반응식
[Cl: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].Cl.[NH2:25][OH:26].CC([O-])=O.[Na+]>CCO>[Cl: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:25][OH:26])[CH3:9]

참가 물질

5

반응물 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866898491-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone

생성물 1

HCID 1364091001-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone oxime수율 102.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone (480 mg, 1.38 mmol), hydroxylamine hydrochloride (478 mg, 6.88 mmol), NaOAc (1.13 g, 13.76 mmol) in EtOH (10 mL) was stirred at RT overnight. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (4:1) to afford 514 mg (94%) of 1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone oxime as white solid. MS (ESI): m/z=364.0 [M+1]+.

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue was purified by SiO2 chromatography
  4. washeluting with petroleum ether/EtOAc (4:1)

출처 및 근거

ORD 기록
ord-a1cc9f81ba3b4417b4f29d1682ffd1ad
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815877B2

반응 노트

불러오는 중…