Sodium periodate → 6-[3-(4-Fluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

HRID 1514677Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[N:14][O:15][C:16]=2/[CH:17]=C/C2C=CC=CC=2)=[N:6][CH:5]=1.I([O-])(=O)(=O)=[O:34].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[N:14][O:15][C:16]=2[CH:17]=[O:34])=[N:6][CH:5]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 6-[3-(4-fluoro-phenyl)-5-((E)-styryl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (3.88 g, 9.01 mmol), osmium(VIII) oxide (57.3 mg, 0.23 mmol), sodium metaperiodate (7.71 g, 36.1 mmol), benzyltriethylammonium chloride (838 mg, 3.61 mmol) in dioxane (60 mL) and water (20 mL) was heated for 15 min at 120° C. in a microwave. Water was then added to the reaction mixture and the resulting mixture extracted with ethyl acetate. The organic extract was then evaporated and the residue purified by chromatography (silica, ethyl acetate:heptane=1:4 to 2:3) to afford the title compound (2.51 g, 78%) as off white oil. MS: m/e=357.2 [M+H]+.

Workup

extractionthe resulting mixture extracted with ethyl acetate
extractionThe organic extract
customwas then evaporated
customthe residue purified by chromatography (silica, ethyl acetate:heptane=1:4 to 2:3)

Sources & evidence

ORD record: ord-ed091781e5a841d8967db3e5f1fe3a8d
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222246B2

Reaction notes

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