Sodium Carbonate → 5-[1-(3-Thiophen-2-yl-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester

HRID 747576

Reaktionsgleichung

Reaktionsgleichung von HRID 747576
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10](=[O:21])[NH:11][CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16](Br)[CH:15]=2)[CH3:13])=[CH:8][CH:9]=1)=[O:4].[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10](=[O:21])[NH:11][CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:23]3[S:22][CH:26]=[CH:25][CH:24]=3)[CH:15]=2)[CH3:13])=[CH:8][CH:9]=1)=[O:4]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 692928715-[1-(3-Bromo-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester

Produkt 1

HCID 692934125-[1-(3-Thiophen-2-yl-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl esterAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a suspension of 10.0 mg (0.0086 mmol) tetrakis(triphenylphosphine)-palladium(0) in 2 ml dry dimethoxyethane, 100 mg (0.272 mmol) 5-[1-(3-Bromo-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester were added and stirred for 10 min at room temperature under nitrogen atmosphere. 52.5 mg (0.410 mmol) thiophene-2-boronic acid in 0.5 ml ethanol and 285 μl (0.570 mmol) of a 2 M aqueous solution of Na2CO3 were added and the mixture was heated in the microwave oven (Emrys Optimizer) at 100° C. for 25 min. After cooling to room temperature, the reaction mixture was filtered and the solid was washed with ethanol. The solvent of the combined filtrates was evaporated. The residue was dissolved in ethyl acetate and washed with brine. The organic phase was dried over magnesium sulfate, the solvent was evaporated and the residue was subjected to silica gel chromatography (ethyl acetate/n-heptane 1:2) to yield 81 mg (0.218 mmol) 5-[1-(3-thiophen-2-yl-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester.

Aufarbeitung

  1. additionwere added
  2. temperaturethe mixture was heated in the microwave oven (Emrys Optimizer) at 100° C. for 25 min
  3. temperatureAfter cooling to room temperature
  4. filtrationthe reaction mixture was filtered
  5. washthe solid was washed with ethanol
  6. customThe solvent of the combined filtrates was evaporated
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. washwashed with brine
  9. dry with materialThe organic phase was dried over magnesium sulfate
  10. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-1e9ef8c9b69b458b8dc9fbbb9969b819
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396944B2

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