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

HRID 340481노트

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HRID 340481 반응식
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]

참가 물질

7

반응물 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 2308893-Bromo-2-chloro-5-nitropyridine

생성물 1

HCID 686190653-Nitrobenzofuro[2,3-b]pyridine수율 52.2%

시약·촉매·용매 2

HCID 587591933375-31-3촉매HCID 962Water용매

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온도
70 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-8792dc0920234e858770a41052831d02
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895585B2

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