Water ethylacetate → 6-(5-Formyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinonitrile

HRID 1514728Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:11]([CH2:12][O:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=2)=[C:10](/[CH:22]=C/C2C=CC=CC=2)[O:9][N:8]=1.I([O-])(=O)(=O)=[O:31].[Na+].C(OCC)(=O)C.O>C(O)(C)(C)C.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH:22]([C:10]1[O:9][N:8]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:11]=1[CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1)=[O:31]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 6-[3-pyridin-2-yl-5-((E)-styryl)-isoxazol-4-ylmethoxy]-nicotinonitrile (0.57 g, 2 mmol), osmium(VIII) oxide solution (0.38 mL of a 2.5% solution in tert-butanol, 0.04 mmol), sodium metaperiodate (1.29 g, 6 mmol), benzyltriethylammonium chloride (0.14 g, 0.6 mmol) in dioxane (13 mL) and water (4.5 mL) was heated in a microwave for 45 min at 120° C. Extractive workup (ethyl acetate/water) was followed by drying of the organic phase over sodium sulfate and filtering. The solvent was evaporated and the residue was triturated with diisopropylether to afford the title compound (0.23 g, 51%) as a white solid. MS: m/e=307.2 [M+H]+.

Workup

dry with materialby drying of the organic phase over sodium sulfate
filtrationfiltering
customThe solvent was evaporated
customthe residue was triturated with diisopropylether

Sources & evidence

ORD record: ord-d48c01973882400b9972a5ba40cc42b9
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222246B2

Reaction notes

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