Phthalaldehyde → 2-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-2,3-dihydro-1H-isoindol-1-one

HRID 42254

반응식

HRID 42254 반응식
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:11]=[C:12]([NH2:19])[C:13]4[CH:14]=[N:15][NH:16][C:17]=4[CH:18]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:20]1([CH:28]=O)[C:21]([CH:26]=[O:27])=[CH:22][CH:23]=[CH:24][CH:25]=1>C(OCC)(=O)C.C(O)(=O)C>[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:18]=[C:17]4[C:13]([CH:14]=[N:15][NH:16]4)=[C:12]([N:19]4[CH2:28][C:20]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[C:26]4=[O:27])[CH:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

5

반응물 2

HCID 4807PhthalaldehydeHCID 582680196-(1H-indol-4-yl)-1H-indazol-4-amine

생성물 1

HCID 445404012-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-2,3-dihydro-1H-isoindol-1-one수율 13.6%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매3회

실험 절차

A mixture of 6-(1H-indol-4-yl)-1H-indazol-4-amine (100 mg, 0.403 mmol) and 1,2-benzenedicarbaldehyde (54 mg, 0.403 mmol) in ethyl acetate (1 ml) and acetic acid (0.25 ml) was stirred under a nitrogen atmosphere at room temperature for 3 h then overnight at room temperature. The reaction mixture was diluted with ethyl acetate (20 ml) and washed with 5% sodium bicarbonate solution (10 ml). The phases were separated, and the aqueous phase was extracted with further ethyl acetate (20 ml). The combined organic extracts (which contained a small amount of insoluble solid) were dried over anhydrous sodium sulphate, filtered and evaporated to give a yellow foam. This was partially dissolved in ethyl acetate (20 ml) and pre-adsorbed on silica (1.5 g). This silica was then added to the top of a 20 g silica SPE cartridge. The cartridge was eluted on a Flashmaster (II) instrument using a gradient of 0-100% ethyl acetate in cyclohexane over 30 min. Appropriate fractions were combined and evaporated to give the title compound (20 mg) as a pale yellow solid.

후처리

  1. customovernight
  2. customat room temperature
  3. washwashed with 5% sodium bicarbonate solution (10 ml)
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with further ethyl acetate (20 ml)
  6. dry with materialwere dried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customto give a yellow foam
  10. additionThis silica was then added to the top of a 20 g silica SPE cartridge
  11. washThe cartridge was eluted on a Flashmaster (II) instrument
  12. customover 30 min
  13. customevaporated

출처 및 근거

ORD 기록
ord-96c609e542224d3793995d64947c00c0
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536169B2

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