Potassium Iodide → N-Benzyl-6,6-dimethyl-1H-pyrano[2,3-f]indole-2,3-dione

HRID 2425370노트

반응식

HRID 2425370 반응식
[CH2:1]([N:8]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[C:11](=[O:12])[C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl[C:29]([CH3:33])([CH3:32])[C:30]#[CH:31].[Cl-].[NH4+]>CN(C=O)C.[Cu](I)I>[CH2:1]([N:8]1[C:18]2[C:13](=[CH:14][C:15]3[O:19][C:29]([CH3:33])([CH3:32])[CH:30]=[CH:31][C:16]=3[CH:17]=2)[C:11](=[O:12])[C:9]1=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 706791-Butyne, 3-chloro-3-methyl-HCID 59134289N-Benzyl-5-hydroxyisatin

생성물 1

HCID 59134332N-Benzyl-6,6-dimethyl-1H-pyrano[2,3-f]indole-2,3-dione수율 8%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
200 °C

실험 절차

Under nitrogen stream, a solution of N-benzyl-5-hydroxyisatin (4.74 g, 18.7 mmol), potassium iodide (5.09 g, 31.8 mmol), potassium carbonate (5.17 g, 37.4 mmol), copper iodide (71 mg, 0.37 mmol) and 3-chloro-3-methyl-1-butyne (4.83 mL, 43.0 mmol) in DMF (47 mL) was stirred at 70° C. for 2 hours. Upon the completion of the reaction, saturated ammonium chloride aqueous solution was added thereto, the resulting solution was extracted with ethyl acetate. The resulting organic phase was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, concentrated and purified by silica gel short column (chloroform). 1,2-Dichlorobenzene (9 mL) was added and the resulting mixture was stirred at 200° C. for 30 minutes. After concentrating the reaction solution, the residue was purified by silica gel column (hexane/ethyl acetate=5/1) to obtain the aimed product (yield: 8%).

후처리

  1. additionwas added
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThe resulting organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified by silica gel short column (chloroform)
  7. addition1,2-Dichlorobenzene (9 mL) was added
  8. concentrationAfter concentrating the reaction solution
  9. customthe residue was purified by silica gel column (hexane/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-325fdad345cf498d815f53c290d6fe5b
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964623B2

반응 노트

불러오는 중…