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

HRID 52011노트

반응식

HRID 52011 반응식
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

참가 물질

5

반응물 4

HCID 6228Dimethylformamide2회HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 19962760Benzyl 5-[(4,6-Dimethoxypyrimidin-2-yl)oxy]2-methylindol-4-carboxylate

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-eb57ac05b267455993677ae9d31e4877
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616537

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