N,N-Dimethylformamide--water (1/1) → 6-Acetyl-5-trifluoromethyl-nicotinonitrile

HRID 545089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 545089
Br[C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:13])[F:12])[C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.[CH3:15][N:16](C=O)C.O>[C-]#N.[C-]#N.[Zn+2].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].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:8]([C:5]1[C:4]([C:11]([F:14])([F:13])[F:12])=[CH:3][C:2]([C:15]#[N:16])=[CH:7][N:6]=1)(=[O:10])[CH3:9]

Komponenten

6

Edukt 2

HCID 21962138N,N-Dimethylformamide--water (1/1)HCID 586455621-(5-Bromo-3-(trifluoromethyl)pyridin-2-yl)ethanone

Produkt 1

HCID 671902526-Acetyl-5-trifluoromethyl-nicotinonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Dissolve 1-(5-bromo-3-(trifluoromethyl)pyridin-2-yl)ethanone (2.67 g, 0.01 mol) in anhydrous DMF/H2O (30.0:0.3 mL) and degas the resulting solution with N2 for 10 minutes. Add Zn(CN)2 (1.17 g, 0.01 mol), Pd2(dba)3 (229 mg, 2.5 mol %) and DPPF (270 mg, 5 mol %). Purge the mixture with N2 for another 10 minutes and heat at 120° C. under N2 atmosphere for 45 minutes. Cool the reaction mixture to room temperature, dilute with water, extract with EtOAc (3×75 mL) and dry (MgSO4). Filter the dried extract and concentrate under vacuum to afford the crude product, which is purified by column chromatography to afford the title product as a yellow solid.

Aufarbeitung

  1. customdegas the resulting solution with N2 for 10 minutes
  2. customPurge the mixture with N2 for another 10 minutes
  3. temperatureCool the reaction mixture to room temperature
  4. additiondilute with water
  5. extractionextract with EtOAc (3×75 mL)
  6. dry with materialdry (MgSO4)
  7. filtrationFilter the dried
  8. extractionextract
  9. concentrationconcentrate under vacuum
  10. customto afford the crude product, which
  11. customis purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c72bae1c6ac94d2d8550f12b05f9a01b
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935702B2

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