Triphenylphosphine → furo[3,2-b]pyridin-3(2H)-one

HRID 1846233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846233
C=[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[O:4][CH2:3]1.C([O:14]C1C(Br)=NC=CC=1)C=C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])=O.[K+]>CN(C=O)C.O.[Cl-].C([N+](CC)(CC)CC)C.CCOC(C)=O.C([O-])(O)=O.[Na+].CC([O-])=O.CC([O-])=O.[Pd+2]>[O:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:2](=[O:14])[CH2:3]1

Komponenten

10

Edukt 4

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 23028574Pyridine, 2-bromo-3-(2-propenyloxy)-HCID 89964775HCID 89964775, Verbindung

Produkt 1

HCID 14199079furo[3,2-b]pyridin-3(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 167845palladium(II) acetateKatalysatorHCID 16211205Tetraethylammonium chloride monohydrateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

3-methylene-2,3-dihydrofuro[3,2-b]pyridine. To a solution of 3-(allyloxy)-2-bromopyridine (1 eq.) in DMF (0.2 M), PPh3 (0.25 eq.), Pd(OAc)2 (0.1 eq), and KOAc (5 eq.), is added, under an argon atmosphere, tetraethyl ammonium chloride hydrate (2 eq.). The flask is purged with argon for 15 min, and the resulting reaction mixture is stirred at 110° C. for 16 h. The reaction progress is monitored by TLC. The reaction mixture is diluted with EtOAc and saturated NaHCO3 solution. The organic layer is separated and dried over Na2SO4, and concentrated. The product that may be thus obtained is purified by column chromatography to afford the title compound.

Aufarbeitung

  1. customThe flask is purged with argon for 15 min
  2. customthe resulting reaction mixture
  3. customThe organic layer is separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe product that may be thus obtained
  7. customis purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-034d2291cbe0402eb05be66bb82eb74d
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952009B2

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