Dimethylformamide → Benzyl 5-[(4,6-Dimethoxypyrimidin-2-yl)oxy]-3-formyl-2-methylindol-4-carboxylate

HRID 52011ノート

反応式

HRID 52011 の反応式
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[N:11]=[C:10]([O:16][C:17]2[CH:25]=[CH:24][C:23]3[NH:22][C:21]([CH3:26])=[CH:20][C:19]=3[C:18]=2[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[N:9]=1.[OH-].[Na+].CN(C)[CH:41]=[O:42]>>[CH3:15][O:14][C:12]1[CH:13]=[C:8]([O:7][CH3:6])[N:9]=[C:10]([O:16][C:17]2[CH:25]=[CH:24][C:23]3[NH:22][C:21]([CH3:26])=[C:20]([CH:41]=[O:42])[C:19]=3[C:18]=2[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[N:11]=1

参加物

5

反応物 4

HCID 6228Dimethylformamide2 回HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 19962760Benzyl 5-[(4,6-Dimethoxypyrimidin-2-yl)oxy]2-methylindol-4-carboxylate

生成物 1

HCID 19962794Benzyl 5-[(4,6-Dimethoxypyrimidin-2-yl)oxy]-3-formyl-2-methylindol-4-carboxylate収率 81.5%

実験手順

0.46 ml of phosphorus oxychloride was dropwise added to 1.8 ml of N,N-dimethylformamide under cooling with ice, and the mixture was stirred for 30 minutes. Then, 2.3 g of benzyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate was dissolved in 10 ml of N,N-dimethylformamide, and the solution was dropwise added to the above mixture under cooling with ice. The mixture was stirred for 30 minutes, and then poured into ice water. An aqueous sodium hydroxide solution was added thereto for adjustment to pH9, followed by extraction with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from isopropyl ether to obtain 2 g (yield: 81.5%) of the desired compound. mp: 148°-149° C.

後処理

  1. temperatureunder cooling with ice
  2. additionthe solution was dropwise added to the above mixture
  3. temperatureunder cooling with ice
  4. stirringThe mixture was stirred for 30 minutes
  5. extractionfor adjustment to pH9, followed by extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe residue obtained by concentration under reduced pressure
  9. customwas crystallized from isopropyl ether

出典と根拠

ORDレコード
ord-eb57ac05b267455993677ae9d31e4877
出典データセット
uspto-grants-1997_04
特許番号
US05616537

反応ノート

読み込み中…