Cesium carbonate → HCID 66745402, Verbindung

HRID 1959415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1959415
Br[C:2]1[N:3]=[C:4]([C:9]2[O:10][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:12][N:13]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[N:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1>CN(C=O)C.[Cu]>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([N:26]2[CH:31]=[CH:30][C:29](=[O:32])[CH:28]=[CH:27]2)=[N:3][C:4]=1[C:9]1[O:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:12][N:13]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 580843425-Bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amineHCID 178418642HCID 178418642, Verbindung

Produkt 1

HCID 66745402HCID 66745402, VerbindungAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a solution of 5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine (150.0 mg, 0.4715 mmol) in DMF (3.000 mL) was added copper (5.992 mg, 0.09430 mmol) and cesium carbonate (307.2 mg, 0.9430 mmol) followed by pyridin-4-ol (448.4 mg, 4.715 mmol) and the reaction mixture heated at 160° C. in the microwave for 1 h. The reaction mixture was filtered and washed with DMF (2 mL). Ethyl acetate and water were added to the filtrate and the layers separated. The aqueous layer was extracted further with ethyl acetate (3×5 mL) and the combined organic extracts were washed with water (3×5 mL). The organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The material was triturated with a mixture of methanol and ether to leave the product. (42.6 mg, 25% yield); 1H NMR (400 MHz, DMSO) d 6.33 (d, 2H), 7.69 (s, 2H), 8.15-8.18 (m, 2H), 8.35 (d, 2H) and 8.78 (s, 1H) ppm; MS (ES+) 333.11

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washwashed with DMF (2 mL)
  3. additionEthyl acetate and water were added to the filtrate
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted further with ethyl acetate (3×5 mL)
  6. washthe combined organic extracts were washed with water (3×5 mL)
  7. dry with materialThe organic extracts were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe material was triturated with a mixture of methanol and ether
  11. customto leave the product

Quellen und Nachweise

ORD-Eintrag
ord-e2ce0f849708446782a86ac32079bb56
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410112B2

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