3-{[6-(4-Bromophenyl)-5-(4-fluorophenyl)furo[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid methyl ester → 3-{[5-(4-Fluorophenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid methyl ester

HRID 2189086노트

반응식

HRID 2189086 반응식
[CH3:1][O:2][C:3](=[O:36])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]2[C:14]3[C:21]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)=[C:20]([C:29]4[CH:34]=[CH:33][C:32](Br)=[CH:31][CH:30]=4)[O:19][C:15]=3[N:16]=[CH:17][N:18]=2)[CH:7]=1>ClCCl.C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:36])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]2[C:14]3[C:21]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)=[C:20]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[O:19][C:15]=3[N:16]=[CH:17][N:18]=2)[CH:7]=1

참가 물질

5

반응물 1

HCID 582801093-{[6-(4-Bromophenyl)-5-(4-fluorophenyl)furo[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid methyl ester

생성물 1

HCID 582801063-{[5-(4-Fluorophenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid methyl ester

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

Dissolve 115 mg (0.21 mmol) of 3-{[6-(4-bromophenyl)-5-(4-fluorophenyl)furo[2,3-d]pyrimidin-4-yl]amino}phenoxy acetic acid methyl ester in 5 ml of dichloromethane and 5 ml of ethyl acetate, and add 22 mg of 10% palladium on activated carbon under argon. Stir the mixture under a hydrogen atmosphere of 3 bar gauge at RT until the starting material has been converted completely. Filter off the catalyst, concentrate the resulting filtrate under reduced pressure and chromatograph the residue on silica gel (eluent: dichloromethane/ethyl acetate 10:1). 27.9 mg (28.3% of theory) of the target compound are obtained as a colourless solid.

후처리

  1. filtrationFilter off the catalyst
  2. concentrationconcentrate the resulting filtrate under reduced pressure and chromatograph the residue on silica gel (eluent: dichloromethane/ethyl acetate 10:1)
  3. custom27.9 mg (28.3% of theory) of the target compound are obtained as a colourless solid

출처 및 근거

ORD 기록
ord-2cd5c9f245ec4b08bb647ebe02e6c09f
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324222B2

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