Potassium Carbonate → [6-Chloro-2-(2-nitrobenzoyl)-1h-indol-3-yl]acetic acid

HRID 396570

반응식

HRID 396570 반응식
[Cl:1][C:2]1[CH:12]=[CH:11][C:5](/[CH:6]=[CH:7]/[C:8]([O-:10])=[O:9])=[C:4]([NH:13]S(C2C=CC=CC=2)(=O)=O)[CH:3]=1.[N+:23]([C:26]1[CH:35]=[CH:34][CH:33]=[CH:32][C:27]=1[C:28](=[O:31])[CH2:29]Br)([O-:25])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6]([CH2:7][C:8]([OH:10])=[O:9])=[C:29]([C:28](=[O:31])[C:27]3[CH:32]=[CH:33][CH:34]=[CH:35][C:26]=3[N+:23]([O-:25])=[O:24])[NH:13]2)=[CH:11][CH:12]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2440252-Bromo-2'-nitroacetophenoneHCID 23003434trans 4-Chloro-2-(phenylsulfonylamino)cinnamate

생성물 1

HCID 23003576[6-Chloro-2-(2-nitrobenzoyl)-1h-indol-3-yl]acetic acid수율 17%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a mixture of polymer-bound trans 4-chloro-2-(phenylsulfonylamino)cinnamate (step 1, 100 mg, 53 μmol) and 2-nitrophenacyl bromide (39 mg, 0.16 mmol) in acetone (3 ml) was added potassium carbonate (37 mg, 0.27 mmol). The mixture was agitated for 18 h. and filtrated. The residual resin was washed with water (20 ml×3), acetone (20 ml×3), dichloromethane (20 ml×3) and THF (20 ml×2) and dried. The resin was diluted with THF (4 ml) and then DBU was added (40 μl, 0.27 mmol). After agitating for 6 h, the resin was filtered off and washed with THF (20 ml×3), acetone (20 ml×3) and dichloromethane (20 ml×3). To the resin was added 95% trifluoroacetic acid in dichloromethane (5 ml) and the mixture was agitated for 3 h. The mixture was filtered and the residue was washed with dichloromethane (20 ml×5). The filtrate was concentrated and the residue was purified by HPLC (MeOH/AcONH4 aquous solution=60/40-90/10) to give 3.2 mg (17%) of the title compound.

후처리

  1. filtrationfiltrated
  2. washThe residual resin was washed with water (20 ml×3), acetone (20 ml×3), dichloromethane (20 ml×3) and THF (20 ml×2)
  3. customdried
  4. additionThe resin was diluted with THF (4 ml)
  5. additionDBU was added (40 μl, 0.27 mmol)
  6. stirringAfter agitating for 6 h
  7. filtrationthe resin was filtered off
  8. washwashed with THF (20 ml×3), acetone (20 ml×3) and dichloromethane (20 ml×3)
  9. additionTo the resin was added 95% trifluoroacetic acid in dichloromethane (5 ml)
  10. stirringthe mixture was agitated for 3 h
  11. filtrationThe mixture was filtered
  12. washthe residue was washed with dichloromethane (20 ml×5)
  13. concentrationThe filtrate was concentrated
  14. customthe residue was purified by HPLC (MeOH/AcONH4 aquous solution=60/40-90/10)

출처 및 근거

ORD 기록
ord-6eadd09bed254e7f9ce398299049b95e
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608070B1

연결된 노트

불러오는 중…