Dimethylformamide → Thiazolo[5,4-b]pyridine-5-carbonitrile

HRID 876797Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 876797
Cl[C:2]1[N:7]=[C:6]2[S:8][CH:9]=[N:10][C:5]2=[CH:4][CH:3]=1.[CH3:11][N:12](C=O)C>[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]>[N:10]1[C:5]2[C:6](=[N:7][C:2]([C:11]#[N:12])=[CH:3][CH:4]=2)[S:8][CH:9]=1

Komponenten

6

Edukt 2

HCID 6228DimethylformamideHCID 23371316HCID 23371316, Verbindung

Produkt 1

HCID 67305386Thiazolo[5,4-b]pyridine-5-carbonitrile

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

To an 8 mL screw cap vial equipped with a magnetic stirring bar were added 5-chlorothiazolo[5,4-b]pyridine (Q-4) (460 mg, 2.7 mmol), Zn(CN)2(316 mg, 2.7 mmol), Pd2(dba)3 (123 mg, 0.13 mmol), DPPF (150 mg, 0.27 mmol) and DMF (5 mL, wet, containing 1% of H2O). The vial was flushed with nitrogen, then sealed with the screw cap. The mixture was stirred at 120° C. for overnight, and then concentrated in vacuo. The resulting residue was purified by chromatography on silica gel to give the title compound (151 mg).

Aufarbeitung

  1. customTo an 8 mL screw cap vial
  2. customequipped with a magnetic stirring bar
  3. customThe vial was flushed with nitrogen
  4. customsealed with the screw
  5. customcap
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7e189a47c0eb447bbd88da5b5e610b71
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987269B2

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