2-Aminophenol → 3-(2-Chlorophenyl)-5-(2-benzoxazolyl)-1-phenyl-1,2-dihydropyridin-2-one

HRID 497850ノート

反応式

HRID 497850 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:24])[N:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=[C:12]([C:14]([O:16][CH3:17])=O)[CH:13]=1.Br[C:26]1[C:27](=O)[N:28](C2C=CC=CC=2)[CH:29]=[C:30](C(OC)=O)[CH:31]=1.ClC1C=CC=CC=1B(O)O.C(Cl)(=O)C(Cl)=O.NC1C=CC=CC=1O>ClCCl.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:24])[N:10]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:11]=[C:12]([C:14]2[O:16][C:17]3[CH:29]=[CH:30][CH:31]=[CH:26][C:27]=3[N:28]=2)[CH:13]=1

参加物

8

反応物 5

HCID 58012-AminophenolHCID 65578Oxalyl chlorideHCID 27343222-Chlorophenylboronic acidHCID 223189503-Bromo-5-methoxycarbonyl-1-phenyl-1,2-dihydropyridin-2-oneHCID 223190963-(2-Chlorophenyl)-5-methoxycarbonyl-1-phenyl-1,2-dihydropyridin-2-one

生成物 1

HCID 223191453-(2-Chlorophenyl)-5-(2-benzoxazolyl)-1-phenyl-1,2-dihydropyridin-2-one

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒4 回

実験手順

19 mg of carboxylate obtained by hydrolyzing the ester group of 3-(2-chlorophenyl)-5-(methoxycarbonyl)-1-phenyl-1,2-dihydropyridin-2-one (synthesized from 3-bromo-5-(methoxycarbonyl)-1-phenyl-1,2-dihydropyridin-2-one and 2-chlorophenylboronic acid in accordance with the method of Referential Example 3) was dissolved in 20 ml of dichloromethane. Under ice-cooling, a solution of 11 mg of oxalyl chloride in dichloromethane was added dropwise thereinto and a catalytic amount of dimethylformamide was added thereto, followed by stirring at room temperature in nitrogen atmosphere for 1 hour. The reaction solution was evaporeted, and the residue was dissolved in dichloromethane. The solution was added dropwise into a solution of 19 mg of 2-aminophenol in dichloromethane under ice-cooling. After heating to room temperature, dichlotomethane was evaporated. To the residue was added 1 ml of polyphosphoric acid, followed by stirring at 180° C. overnight. After cooling to room temperature, the reaction mixture was neutralized with 1N aqueous solution of sodium hydroxide and saturated aqueous solution of sodium hydrogen carbonate under ice-cooling. The mixture was extracted with ethyl acetate, and the resulting 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 3 mg of the title compound as white crystals.

後処理

  1. temperatureUnder ice-cooling
  2. temperaturecooling
  3. temperatureAfter heating to room temperature
  4. customdichlotomethane was evaporated
  5. additionTo the residue was added 1 ml of polyphosphoric acid
  6. stirringby stirring at 180° C. overnight
  7. temperatureAfter cooling to room temperature
  8. temperaturecooling
  9. extractionThe mixture was extracted with ethyl acetate
  10. washthe resulting organic layer was washed with brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated
  13. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate system)

出典と根拠

ORDレコード
ord-d0c6345a24d34d52b117cb36e11137e1
出典データセット
uspto-grants-2005_09
特許番号
US06949571B2

反応ノート

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