Nitrogen → 6-Acetyl-4-chloro-3'-fluoro-3-methylbiphenyl-2-carbonitrile

HRID 510819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510819
FC(F)(F)S(O[C:7]1[C:12]([C:13](=[O:15])[CH3:14])=[CH:11][C:10]([Cl:16])=[C:9]([CH3:17])[C:8]=1[C:18]#[N:19])(=O)=O.[F:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1.N#N>C1(C)C=CC=CC=1.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>[C:13]([C:12]1[CH:11]=[C:10]([Cl:16])[C:9]([CH3:17])=[C:8]([C:18]#[N:19])[C:7]=1[C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([F:22])[CH:28]=1)(=[O:15])[CH3:14]

Komponenten

7

Edukt 3

HCID 947NitrogenHCID 27339863-Fluorophenylboronic acidHCID 583686446-Acetyl-4-chloro-2-cyano-3-methylphenyl trifluoromethanesulfonate

Produkt 1

HCID 583684696-Acetyl-4-chloro-3'-fluoro-3-methylbiphenyl-2-carbonitrileAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A biphasic solution of 6-acetyl-4-chloro-2-cyano-3-methylphenyl trifluoromethanesulfonate (2.54 g, 7.4 mmol) and (3-fluorophenyl)boronic acid (1.6 g, 11 mmol) in toluene (70 mL) and saturated sodium bicarbonate (70 mL) was bubbled with N2 to degas. After tetrakis(triphenylphosphine)palladium(0) (0.43 g, 0.37 mmol) was added, the mixture was bubbled with N2 for 5 min more and then heated at 80° C. for 2 hours. After cool to room temperature, the mixture was diluted with ethyl acetate. The layers were separated and the aq. layer was extracted with more ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified on silica gel column, eluting with 0 to 40% ethyl acetate in hexane, to give the desired product (2.1 g, 99%). LCMS calculated for C16H12ClFNO (M+H)+: m/z=288.1. found: 288.1.

Aufarbeitung

  1. customto degas
  2. customthe mixture was bubbled with N2 for 5 min more
  3. temperatureAfter cool to room temperature
  4. additionthe mixture was diluted with ethyl acetate
  5. customThe layers were separated
  6. extractionthe aq. layer was extracted with more ethyl acetate
  7. washThe combined extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified on silica gel column
  12. washeluting with 0 to 40% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-900856663b4b420ca7875ac472ae52b9
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096600B2

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