Phenol → 3-Nitrobenzofuro[2,3-b]pyridine

HRID 1620088Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[C:7]1([OH:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN(C)C(=O)C.Br[C:21]1[C:22](Cl)=[N:23][CH:24]=[C:25]([N+:27]([O-:29])=[O:28])[CH:26]=1>[Pd].C(O)(=O)C.O>[N+:27]([C:25]1[CH:26]=[C:21]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[O:13][C:22]2=[N:23][CH:24]=1)([O-:29])=[O:28]

Participants

Conditions

Temperature: 70 °C

Procedure

Potassium carbonate (87 mg) and phenol (47 mg) were added to an N,N-dimethylacetamide (1 ml) solution containing 3-bromo-2-chloro-5-nitropyridine (100 mg), followed by stirring at 70° C. for 3 hours. Acetic acid palladium (20 mg) was added in a nitrogen atmosphere, followed by stirring at 100° C. for 3.5 hours. Water was added, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, hexane and ethyl acetate were added to the obtained residue, an insoluble precipitate was collected by filtration, and a light yellow solid of 3-nitrobenzofuro[2,3-b]pyridine (47.1 mg) was thus obtained.

Workup

stirringby stirring at 100° C. for 3.5 hours
extractionfollowed by extraction with ethyl acetate
washThe resultant was washed with saturated saline
dry with materialdried over anhydrous sodium sulfate
distillationSubsequently, the solvent was distilled away under reduced pressure, hexane and ethyl acetate
additionwere added to the obtained residue
filtrationan insoluble precipitate was collected by filtration

Sources & evidence

ORD record: ord-14d5db1443ca4b5586d393a1e6d06069
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772320B2

Reaction notes

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