Tetrahydrofuran → 5-Bromo-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 2095857노트

반응식

HRID 2095857 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([C:15]#[N:16])[C:9]2=[O:17])=[CH:4][CH:3]=1.O1CCCC1.[Br:23]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>C(#N)C.C(OCC)(=O)C>[Br:23][C:12]1[CH:11]=[C:10]([C:15]#[N:16])[C:9](=[O:17])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:13]=1[CH3:14]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 669689251-(4-Fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

생성물 1

HCID 581585675-Bromo-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile수율 86%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

To a solution of 1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (1 g, 4.05 mmol) in acetonitrile (10 mL)/tetrahydrofuran (5 mL) was added N-bromosuccinimide (792 mg, 4.46 mmol), and the mixture was stirred at 60° C. overnight. After cooling to room temperature, saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was washed with diethyl ether and collected by filtration to give the title compound (1.07 g, 86%) as a slightly yellow solid.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted 3 times with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure
  7. washThe obtained residue was washed with diethyl ether
  8. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-ebf3ebaf7671419a91cdc7b0b827824e
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445509B2

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