Potassium Carbonate → Ethyl 5-(3-fluoro-4-(trifluoromethyl)phenyl)-4-methylisoxazole-3-carboxylate

HRID 1510457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1510457
[F:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].Br[C:22]1[O:26][N:25]=[C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:23]=1[CH3:32].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.C(OCC)(=O)C.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>[F:1][C:2]1[CH:3]=[C:4]([C:22]2[O:26][N:25]=[C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:23]=2[CH3:32])[CH:5]=[CH:6][C:7]=1[C:8]([F:9])([F:10])[F:11]

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 467390543-Fluoro-4-(trifluoromethyl)phenylboronic acid pinacol esterHCID 58828802Ethyl 5-bromo-4-methyl-1,2-oxazole-3-carboxylate

Produkt 1

HCID 66792925Ethyl 5-(3-fluoro-4-(trifluoromethyl)phenyl)-4-methylisoxazole-3-carboxylateAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium(0) (139 mg, 0.121 mmol) was added to a suspension of 2-(3-fluoro-4-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (350 mg, 1.21 mmol), ethyl 5-bromo-4-methylisoxazole-3-carboxylate (282 mg, 1.21 mmol) and potassium carbonate (334 mg, 2.413 mmol) in DME and water mix. The reaction mixture was sealed in a microwave vial and heated at 100° C. for 2 hours, after which time, the reaction was allowed to cool. The reaction mixture was then diluted with ethyl acetate and washed with water. The aqueous layer was then extracted with ethyl acetate, the organics combined, washed with brine and dried over magnesium sulfate, filtered and concentrated in vacuo. the resulting residue was purified by silica gel chromatography, eluting with heptane to 40% ethylacetate in heptane, to afford ethyl 5-(3-fluoro-4-(trifluoromethyl)phenyl)-4-methylisoxazole-3-carboxylate (196 mg, 0.62 mmol).

Aufarbeitung

  1. additionmix
  2. customThe reaction mixture was sealed in a microwave vial
  3. temperatureto cool
  4. washwashed with water
  5. extractionThe aqueous layer was then extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customthe resulting residue was purified by silica gel chromatography
  11. washeluting with heptane to 40% ethylacetate in heptane

Quellen und Nachweise

ORD-Eintrag
ord-b7e05552301844e8865bee8eeb3f915e
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211927B2

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