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

HRID 2409040Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 60 °C

Procedure

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]+.

Workup

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

Sources & evidence

ORD record: ord-80b21df78f78489e9794a8fa51ef71fa
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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