Methyl Acetate → 3-Bromomethyl-7-(2,6-difluorobenzyl)-4,7-dihydro-5-isobutyryl-4-oxo-2-phenylthieno[2,3-b]pyridine

HRID 2304879

반응식

HRID 2304879 반응식
[F:1][C:2]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:3]=1[CH2:4][N:5]1[CH:10]=[C:9]([C:11](=[O:15])[CH:12]([CH3:14])[CH3:13])[C:8](=[O:16])[C:7]2[C:17]([CH3:26])=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[S:19][C:6]1=2.[Br:32]N1C(=O)CCC1=O.CC(CC(C)C)C#N.C(OC)(=O)C>O>[Br:32][CH2:26][C:17]1[C:7]2[C:8](=[O:16])[C:9]([C:11](=[O:15])[CH:12]([CH3:14])[CH3:13])=[CH:10][N:5]([CH2:4][C:3]3[C:2]([F:1])=[CH:30][CH:29]=[CH:28][C:27]=3[F:31])[C:6]=2[S:19][C:18]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

참가 물질

6

반응물 4

HCID 6584Methyl AcetateHCID 67184N-bromobutanimideHCID 120498617-(2,6-Difluorobenzyl)-4,7-dihydro-5-isobutyryl-3-methyl-4-oxo-2-phenylthieno[2,3-b]pyridineHCID 218816762,4-Dimethylpentanenitrile

생성물 1

HCID 184586143-Bromomethyl-7-(2,6-difluorobenzyl)-4,7-dihydro-5-isobutyryl-4-oxo-2-phenylthieno[2,3-b]pyridine수율 89.9%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

7-(2,6-Difluorobenzyl)-4,7-dihydro-5-isobutyryl-3-methyl-4-oxo-2-phenylthieno[2,3-b]pyridine (10 g), N-bromosuccinimide (4.86 g), 2,2′-azobis(2,4-dimethylvaleronitrile (0.56 g) and methyl acetate (100 ml) were mixed and the reaction mixture was heated under reflux for 2 hours. The reaction mixture was allowed to cool with stirring over a period of 2 hours, water (50 ml) was added and then the mixture was stirred with cooling on ice for 1.5 hours. The crystal precipitated was recovered by a filtration, washed with an ice-cooled methyl acetate (30 ml) and water (30 ml), dried in vacuo at 40° C. for 6 hours to obtain the title compound (10.61 g, 87.1%).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. stirringthe mixture was stirred
  5. temperaturewith cooling on ice for 1.5 hours
  6. customThe crystal precipitated
  7. filtrationwas recovered by a filtration
  8. washwashed with an ice-
  9. temperaturecooled methyl acetate (30 ml) and water (30 ml)
  10. customdried in vacuo at 40° C. for 6 hours

출처 및 근거

ORD 기록
ord-0e329bda27494077b0c0284bc2fff874
출처 데이터셋
uspto-grants-2002_08
특허 번호
US06437132B2

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