3-Methoxy-2-pyridone → HCID 59586725, compound

HRID 218506Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4](=[O:9])[NH:5][CH:6]=[CH:7][CH:8]=1.CC(C)([O-])C.[K+].[F:16][CH:17]([F:29])[O:18][C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1F>CS(C)=O.ClCCl>[F:16][CH:17]([F:29])[O:18][C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]1=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

302 mg (2.41 mmol) of 3-methoxypyridone are dissolved in 8.2 ml of anhydrous dimethyl sulfoxide and admixed with 325 mg (2.89 mmol) of potassium tert-butoxide. After 30 min, 500 mg (2.41 mmol) of 2-(difluoromethoxy)-1-fluoro-4-nitrobenzene are added and the mixture is heated to 80° C. for 20 h. The reaction solution is diluted with dichloromethane and washed with water and 1N hydrochloric acid. After the organic phase has been dried over sodium sulfate, it is filtered and concentrated to dryness under reduced pressure. The residue is dissolved in dimethyl sulfoxide and purified by preparative HPLC with a water/acetonitrile gradient. The product fractions are combined and concentrated to dryness under reduced pressure. This affords 207 mg (28% of theory) of the desired product.

Workup

washwashed with water and 1N hydrochloric acid
dry with materialAfter the organic phase has been dried over sodium sulfate, it
filtrationis filtered
concentrationconcentrated to dryness under reduced pressure
dissolutionThe residue is dissolved in dimethyl sulfoxide
custompurified by preparative HPLC with a water/acetonitrile gradient
concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-613ac57eb69c41b59e8642ec5330dd1f
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198267B2

Reaction notes

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