Citric Acid → N-(2-cyano-5-phenylphenyl)-5-phenylpyridine-3-carboxamide

HRID 454516ノート

反応式

HRID 454516 の反応式
[C:1]1(OB=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl[C:19]1[CH:20]=[CH:21][C:22]([C:40]#[N:41])=[C:23]([NH:25][C:26]([C:28]2[CH:29]=[N:30][CH:31]=[C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:33]=2)=[O:27])[CH:24]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:40]([C:22]1[CH:21]=[CH:20][C:19]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:24][C:23]=1[NH:25][C:26]([C:28]1[CH:29]=[N:30][CH:31]=[C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:33]=1)=[O:27])#[N:41]

参加物

9

反応物 4

HCID 311Citric AcidHCID 62657Potassium Phosphate, TribasicHCID 14438906HCID 14438906、化合物HCID 58508508N-(5-chloro-2-cyanophenyl)-5-phenylpyridine-3-carboxamide

生成物 1

HCID 58508437N-(2-cyano-5-phenylphenyl)-5-phenylpyridine-3-carboxamide収率 102.2%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒2 回HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl触媒2 回HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Phenylboranic acid (88 mg), tripotassium phosphate (0.28 g), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (2.5 mg), and palladium(II) acetate (2.7 mg) were added to a toluene (3.0 mL) suspension of N-(5-chloro-2-cyanophenyl)-5-phenylpyridine-3-carboxamide (0.20 g), followed by heating to reflux under a nitrogen atmosphere for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (2.5 mg) and palladium(II) acetate (2.7 mg) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 6 hours. After cooling the reaction mixture to room temperature, ethyl acetate and a 10% aqueous solution of citric acid were added thereto, and the insoluble substance was removed by filtration. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.23 g of N-(2-cyano-5-phenylphenyl)-5-phenylpyridine-3-carboxamide as a light yellow solid.

後処理

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 1 hour and 30 minutes
  3. temperatureby heating
  4. temperatureto reflux under a nitrogen atmosphere for 6 hours
  5. temperatureAfter cooling the reaction mixture to room temperature
  6. customthe insoluble substance was removed by filtration
  7. customThe organic layer was separated
  8. washwashed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. additionDiisopropyl ether was added to the obtained residue
  12. filtrationthe solid substance was collected by filtration

出典と根拠

ORDレコード
ord-db590438e2744b75b530e827c9701dc6
出典データセット
uspto-grants-2013_07
特許番号
US08492582B2

反応ノート

読み込み中…