Dimethylacetamide → {1-[4-(6-cyano-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 1037205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1037205
[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[C:24](Br)[CH:25]=4)[O:20][C:19]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C[C:38]([N:40](C)C)=O>[C-]#N.[Zn+2].[C-]#N>[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:38]#[N:40])[CH:25]=4)[O:20][C:19]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 31374DimethylacetamideHCID 67067709{1-[4-(6-Bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Produkt 1

HCID 67067657{1-[4-(6-cyano-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11186Zinc cyanide (Zn(CN)2)Katalysator

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

{1-[4-(6-Bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (92 mg, 0.17 mmol), zinc (II) cyanide (40 mg, 0.34 mmol) and tetrakis(triphenyphosphine)palladium(0) (20 mg, 0.017 mmol) were suspended in DMA (2 mL) in a microwave vial. The vial was sealed, evacuated and flushed twice with nitrogen. The mixture was heated in a microwave at 150° C. for 30 min. The resulting mixture was allowed to cool to RT, partitioned between ethyl acetate (40 mL) and water (20 mL) and the phases separated. The organic layer was washed with brine (20 mL), dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was subjected to flash chromatography (SiO2, 20% ethyl acetate in cyclohexane) to afford the title compound as a white solid (45 mg, 54%). LCMS (Method B): RT=4.76 min, [M+Na]+=515.

Aufarbeitung

  1. customThe vial was sealed
  2. customevacuated
  3. customflushed twice with nitrogen
  4. temperatureto cool to RT
  5. custompartitioned between ethyl acetate (40 mL) and water (20 mL)
  6. customthe phases separated
  7. washThe organic layer was washed with brine (20 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d21b3ee55f9d4e9c9c802861c6829ffa
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546376B2

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