Water → 1-(2-Ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)ethanone

HRID 2389924Notes

Reaction equation

[N+]([C:4]1[CH:9]=[C:8]([N+]([O-])=O)[CH:7]=[CH:6][C:5]=1[O-:13])([O-])=O.[NH2:14][N+:15]1[CH:20]=[CH:19][C:18]2[O:21][CH2:22][CH2:23][C:17]=2[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CC(=O)C#CCC.O>CN(C)C=O>[CH2:8]([C:9]1[C:4]([C:5](=[O:13])[CH3:6])=[C:16]2[C:17]3[CH2:23][CH2:22][O:21][C:18]=3[CH:19]=[CH:20][N:15]2[N:14]=1)[CH3:7]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 5-amino-2,3-dihydrofuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolate (2.00 g, 6.24 mmol), potassium carbonate (1.21 g, 8.75 mmol) and 3-hexyn-2-one (0.750 mL, 6.87 mmol) in dimethylformamide (30 mL) was stirred at 40° C. for 16 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→40/60) to give the title compound (314 mg, yield 22%).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→40/60)

Sources & evidence

ORD record: ord-ce93be09c2a048fdbd74b989863cf97e
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273761B2

Reaction notes

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