Triphenylphosphine → 1-(4-nitro-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide

HRID 384975

Reaktionsgleichung

Reaktionsgleichung von HRID 384975
[O:1]=[C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][NH:3]1.[N+:17]([C:20]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:21]=1[CH2:22][CH2:23][C:24]2=O)([O-:19])=[O:18].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>CN(C=O)C.O>[N+:17]([C:20]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:21]=1[CH2:22][CH2:23][CH:24]2[N:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[O:9])[C:2]1=[O:1])([O-:19])=[O:18]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 905634-Nitroindan-1-oneHCID 35448842-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamideHCID 5363146Diisopropyl azodicarboxylate

Produkt 1

HCID 498038661-(4-nitro-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamideAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide (8.0 g, 1.0 eq) in dry DMF (30 mL) was added 4-nitro-2,3-dihydro-1H-inden-1-one (1.2 eq) and PPh3 (3.0 eq), then added DIAD (3.0 eq) under N2 atmosphere. Then the mixture was stirred at room temperature overnight. At the end of reaction, water was added and extracted with ethyl acetate. The combined organic layer was washed with brine and dried over MgSO4, filtrated and evaporated to give the crude product, which was purified by Flash Column (PE:EtOAc=1:2), concentrated the crude product, and recrystallized by EtOAc to give 1-(4-nitro-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide (3.5 g, 21%). MS (ESI) 377.0 (M+H); 1H NMR (300 MHz, CDCl3) δ 12.22 (s, 1H), 8.62 (m, 1H), 8.53 (m, 2H), 8.24 (m, 1H), 7.67 (m, 2H), 7.49 (m, 2H), 6.75 (m, 1H), 6.50 (m, 1H), 3.71 (m, 1H), 3.57 (m, 1H), 2.97 (m, 1H), 2.21 (m, 2H).

Aufarbeitung

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltrated
  6. customevaporated
  7. customto give the crude product, which
  8. customwas purified by Flash Column (PE:EtOAc=1:2)
  9. concentrationconcentrated the crude product
  10. customrecrystallized by EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-c5832e318d6e4d9ba22e7f70daa9f1c3
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367836B2

Verknüpfte Notizen

Wird geladen…