Aniline → 3-Phenylamino-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one

HRID 229681

反応式

HRID 229681 の反応式
Br[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.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:22]1([NH:21][C:2]2[C:3](=[O:20])[N:4]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[CH:7]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

7

反応物 3

HCID 6115AnilineHCID 223190653-Bromo-1-phenyl-5-(pyridin-2-yl)-1,2-dihydropyridin-2-oneHCID 23676156Sodium t-butoxide

生成物 1

HCID 223191743-Phenylamino-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one収率 85.5%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

53 mg of 3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one and 23 mg of aniline were dissolved in 10 ml of toluene, to which 2 mg of palladium acetate, 7 mg of 1,1′-bis(diphenylphosphino)ferrocene and 23 mg of sodium tert-butoxide were added, and the mixture was stirred at 110° C. for a night. The reaction solution was cooled to room temperature, filtered by silica gel and washed with ether, and the filtrate was distilled under a vacuum to remove the solvent. The residue was refined by silica gel chromatography (NH silica) (hexane/ethyl acetate-based solvent), to obtain 47 mg of the subject compound.

後処理

  1. additionwere added
  2. temperatureThe reaction solution was cooled to room temperature
  3. filtrationfiltered by silica gel
  4. washwashed with ether
  5. distillationthe filtrate was distilled under a vacuum
  6. customto remove the solvent

出典と根拠

ORDレコード
ord-7206d9e79fbb4e758e4b3506020abccd
出典データセット
uspto-grants-2009_07
特許番号
US07563811B2

関連ノート

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