Potassium Carbonate → 5-(2-fluorophenyl)-1-[(6-methylpyridin-3-yl)sulfonyl]-1H-pyrrole-3-carbaldehyde

HRID 1962579Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1962579
Cl[C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])=[CH:14][C:13]([CH:23]=[O:24])=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:25]B(O)O.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[F:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:15]1[N:11]([S:8]([C:5]2[CH:6]=[N:7][C:2]([CH3:25])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH:12]=[C:13]([CH:23]=[O:24])[CH:14]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 516892Sodium BicarbonateHCID 86630978HCID 86630978, Verbindung

Produkt 1

HCID 866309795-(2-fluorophenyl)-1-[(6-methylpyridin-3-yl)sulfonyl]-1H-pyrrole-3-carbaldehydeAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Under an argon atmosphere, a mixture of 1-[(6-chloropyridin-3-yl)sulfonyl]-5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (365 mg), methylboronic acid (90 mg), tetrakis(triphenylphosphine)palladium (116 mg), potassium carbonate (691 mg) and 1,4-dioxane (25 mL) was stirred at 80° C. for 3 days. The reaction mixture was poured into saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→1:1) to give the title compound as a yellow solid (yield 134 mg, 39%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-a6647754649f48a69e36518dd613bfd5
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415368B2

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