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 2189086Notes

Reaction equation

HRID 2189086 reaction equation
[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

Participants

5

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2cd5c9f245ec4b08bb647ebe02e6c09f
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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