Sodium Carbonate → 2-Cyclopropyl-6-(trifluoromethyl)nicotinaldehyde

HRID 1626523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1626523
Cl[C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH:14]1(B(O)O)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:14]1([C:2]2[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[CH2:16][CH2:15]1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 467399062-Chloro-6-(trifluoromethyl)pyridine-3-carbaldehyde

Produkt 1

HCID 866644002-Cyclopropyl-6-(trifluoromethyl)nicotinaldehydeAusbeute 71,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2-Chloro-6-(trifluoromethyl)nicotinaldehyde (176 mg, 0.840 mmol), cyclopropylboronic acid (152 mg, 1.76 mmol), sodium carbonate (267 mg, 2.52 mmol) and tetrakis(triphenylphosphine)palladium (0) (48.5 mg, 0.0420 mmol) were combined, diluted with toluene (2 mL) and water (200 μL). The reaction vial was purged with argon, heated to 90° C. and stirred for 24 hours. The reaction was allowed to cool, loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield 2-cyclopropyl-6-(trifluoromethyl)nicotinaldehyde (130 mg, 0.604 mmol, 71.9% yield).

Aufarbeitung

  1. customThe reaction
  2. customvial was purged with argon
  3. temperatureto cool
  4. washeluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2e9856b3cd7545e098d45477bcf06e59
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785445B2

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