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

HRID 2095857ノート

反応式

HRID 2095857 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ebf3ebaf7671419a91cdc7b0b827824e
出典データセット
uspto-grants-2013_05
特許番号
US08445509B2

反応ノート

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