Dimethylformamide → HCID 53946632, Verbindung

HRID 1459633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1459633
CN(C=O)C.I[C:7]1[C:12]([CH3:13])=[N:11][CH:10]=[CH:9][N:8]=1.[CH:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)=[O:15].CCN(CC)CC>CC([O-])=O.CC([O-])=O.[Pd+2].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(Cl)(Cl)Cl>[CH3:13][C:12]1[C:7]([C:19]2[CH:20]=[CH:21][C:16]([CH:14]=[O:15])=[CH:17][CH:18]=2)=[N:8][CH:9]=[CH:10][N:11]=1

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 5910734-Formylphenylboronic AcidHCID 108786642-IODO-3-METHYLPYRAZINE

Produkt 1

HCID 53946632HCID 53946632, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a 100 ml round bottomed flask with stirring bar and an argon inlet was added Pd(OAc)2 (0.036 g, 0.15 mmol), bisdiphenylphosphinoferrocene (DPPF, 0.12 g, 0.2 mmol), and 15 ml of DMF were heated to 50° for 15 minutes. Cooled the reaction to room temperature then added 2-iodo-3-methyl-pyrazine (1.2 g, 5.4 mmol)(5). (a prep from Albert Hirschberg et al. J.Org. Chem. Jun.,1961 p1907-1912) and 4-formylbenzenboronic acid (0.90 g, 6.0 mmol) and Et3N (1.05 ml, 7.5 mmol). The mixture was heated to 90° C. for 10 h. Removed solvent in vacuo, taken up with CHCl3 and washed with diluted NH4OH. The organic layer was dried (MgSO4), filtered and concentrated to yield a black oil. This material was chromatographed (silica gel, 30% EtOAc/Hexane) to afford the title product.

Aufarbeitung

  1. temperaturewere heated to 50° for 15 minutes
  2. temperatureCooled
  3. customthe reaction to room temperature
  4. washwashed with diluted NH4OH
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a black oil
  9. customThis material was chromatographed (silica gel, 30% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ae9eb7c78185463e975496bacac934ba
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05854264

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