Hydrochloric Acid → 1-(4-Isopropoxyphenyl)-1H-indole-2,3-dione

HRID 1374965

반응식

HRID 1374965 반응식
C(N(CC)CC)C.[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[C:9]1=[O:18].[CH:19]([O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)([CH3:21])[CH3:20].Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:19]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[C:9]2=[O:18])=[CH:25][CH:24]=1)([CH3:21])[CH3:20]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 7054IsatinHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 36987264-Isopropoxybenzeneboronic acid

생성물 1

HCID 210793831-(4-Isopropoxyphenyl)-1H-indole-2,3-dione수율 39.7%

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

실험 절차

A solution of triethylamine (28 g, 272 mmol) in CH2Cl2 (250 mL) was added to a mixture of 1H-indole-2,3-dione (10.0 g, 68 mmol), 4-isopropoxyphenylboronic acid (13.4 g, 75 mmol) and copper (II) acetate (5.0 g, 27 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The crude mixture was then treated with 1M HCl (3×350 mL), followed by aqueous saturated NaHCO3 solution (3×350 mL). The resulting organic faction was concentrated in vacuo and the residue was dissolved in CH2Cl2, dried over MgSO4, concentrated in vacuo, and re-suspended in CH2Cl2. The suspension was filtered and the filtrate was concentrated in vacuo. The crude product was recrystallized from a mixture of toluene/hexane (3:1), giving the desired product (7.6 g, 27 mmol).

후처리

  1. concentrationThe resulting organic faction was concentrated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. filtrationThe suspension was filtered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe crude product was recrystallized from a mixture of toluene/hexane (3:1)

출처 및 근거

ORD 기록
ord-762a474162cf4bfc98323d7edd6e7cb5
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07166635B2

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