Acetohydroxamic Acid → 7-(4-Methylpyridin-3-yl)isoxazolo[4,5-b]pyridin-3-amine

HRID 871152Notes

Reaction equation

F[C:2]1[C:3]([C:15]#[N:16])=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[CH3:14].[OH:17][NH:18]C(=O)C.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:14][C:13]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[C:7]1[CH:6]=[CH:5][N:4]=[C:3]2[C:15]([NH2:16])=[N:18][O:17][C:2]=12

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3′-fluoro-4-methyl-3,4′-bipyridine-2′-carbonitrile (0.057 g, 0.267 mmol), N-hydroxyacetamide (0.060 g, 0.802 mmol), and potassium carbonate (0.222 g, 1.604 mmol) in DMF (Ratio: 7.0, Volume: 1.170 ml) and water (Ratio: 1.000, Volume: 0.167 ml) was stirred at 80° C. for 3 hr. The reaction mixture was filtered through a disposable fritted funnel. The filter cake was washed with EtOAc. Layers in the filtrate were separated and the aqueous phase was extracted with EtOAc (3×). The organic phases were combined, dried over Na2SO4, filtered, concentrated, and further dried under high vacuum to afford the title compound as a brown solid (49 mg, 0.206 mmol, 77% yield). ESI MS (M+H)+=227.1.

Workup

filtrationThe reaction mixture was filtered through a disposable fritted funnel
washThe filter cake was washed with EtOAc
customLayers in the filtrate were separated
extractionthe aqueous phase was extracted with EtOAc (3×)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customfurther dried under high vacuum

Sources & evidence

ORD record: ord-75dfc266b99e43dfa481e921f2f60f87
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969586B2

Reaction notes

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