5-{4-[2-(Indol-1-yl)ethoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dione → 5-((4-(2-(1H-Indol-1-yl)ethoxy)phenyl)methyl)-2,4-thiazolidinedione

HRID 1953644노트

반응식

HRID 1953644 반응식
[N:1]1([CH2:10][CH2:11][O:12][C:13]2[CH:45]=[CH:44][C:16]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[N:20](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:19]3=[O:43])=[CH:15][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H][H]>O1CCOCC1.[Pd]>[N:1]1([CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:43])=[CH:44][CH:45]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

5

반응물 2

HCID 232983005-{4-[2-(Indol-1-yl)ethoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dioneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 1540055-((4-(2-(1H-Indol-1-yl)ethoxy)phenyl)methyl)-2,4-thiazolidinedione수율 85.9%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 312751,4-Dioxane용매

실험 절차

A solution of 2.05 g of 5-{4-[2-(indol-1-yl)-ethoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dione (prepared as described in Preparation 14) in 100 ml of dioxane was stirred in an atmosphere of hydrogen and in the presence of 3.1 g of 10% w/w palladium-on-charcoal, first at room temperature for 30 minutes, then at 60° C. for 2 hours and then at 80° C. for 3 hours. At the end of this time, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated by evaporation under reduced pressure. The concentrate was then purified by column chromatography through silica gel, using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.06 g of the title compound, melting at 42.3-44.6° C.

후처리

  1. waitat 80° C. for 3 hours
  2. filtrationAt the end of this time, the reaction mixture was filtered
  3. customto remove the catalyst
  4. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  5. customThe concentrate was then purified by column chromatography through silica gel
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-ae40857879fa433e8794a745c54ad34c
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06117893

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