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

HRID 396570

反応式

HRID 396570 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6eadd09bed254e7f9ce398299049b95e
出典データセット
uspto-grants-2003_08
特許番号
US06608070B1

関連ノート

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