1-Phenyl-1,4-pentanedione → 3-(2-Methyl-5-phenylpyrrol-1-yl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one

HRID 547726

反応式

HRID 547726 の反応式
[NH2:1][C:2]1[C:3](=[O:20])[N:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1.[C:21]1([C:27](=O)[CH2:28][CH2:29][C:30](=O)[CH3:31])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>[CH3:31][C:30]1[N:1]([C:2]2[C:3](=[O:20])[N:4]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[CH:7]=2)[C:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:28][CH:29]=1

参加物

6

反応物 3

HCID 1363711-Phenyl-1,4-pentanedioneHCID 516892Sodium BicarbonateHCID 223191193-Amino-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one

生成物 1

HCID 223192353-(2-Methyl-5-phenylpyrrol-1-yl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one収率 31.3%

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 1140Toluene溶媒

実験手順

25 mg of 3-amino-1-phenyl-5-(2-pyridyl)-1,2-dihydropyridin-2-one was dissolved in 10 ml of toluene. To the mixture were added 20 mg of 1-phenyl-1,4-pentandione and 0.2 mg of p-toluenesulfonate (hydrate), followed by heating under reflux for 1 hour. After cooling to room temperature, the reaction mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate, followed by extracting with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate system), to give 12 mg of the title compound.

後処理

  1. temperatureby heating
  2. temperatureunder reflux for 1 hour
  3. extractionby extracting with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate system)

出典と根拠

ORDレコード
ord-783f50cec41745ea97a69fd5a54bdf6e
出典データセット
uspto-grants-2011_05
特許番号
US07939549B2

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