Potassium Carbonate → 4-Methylene-6-[1-(3-pyridyl)pyrazol-4-yl]-2,3-dihydropyrano[3,2-b]pyridine

HRID 1478548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478548
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CC1(C)C(C)(C)OB([C:34]2[CH:35]=[N:36][N:37]([C:39]3[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=3)[CH:38]=2)O1.Br[C:47]1[N:52]=[C:51]2[C:53](=[CH2:57])[CH2:54][CH2:55][O:56][C:50]2=[CH:49][CH:48]=1>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CN(C=O)C.[Pd](Cl)Cl.O.CCOC(C)=O>[CH2:57]=[C:53]1[C:51]2=[N:52][C:47]([C:34]3[CH:35]=[N:36][N:37]([C:39]4[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=4)[CH:38]=3)=[CH:48][CH:49]=[C:50]2[O:56][CH2:55][CH2:54]1

Komponenten

10

Edukt 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 574162183-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyridineHCID 584840716-bromo-4-methylene-3,4-dihydro-2H-pyrano[3,2-b]pyridine

Produkt 1

HCID 900430134-Methylene-6-[1-(3-pyridyl)pyrazol-4-yl]-2,3-dihydropyrano[3,2-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 24290Palladium ChlorideKatalysatorHCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

137 mg (0.78 mmol) of palladium chloride, 948 mg (3.62 mmol) of triphenylphosphine, 356 mg (25.8 mmol) of K2CO3 and 3.54 g (11.89 mmol) of n-Bu4NCl in 30 ml of DMF were heated under 105° C. for 10 min under N2. 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyrazol-1-yl]pyridine (3.5 g, 12.92 mmol) and 6-bromo-4-methylene-2,3-dihydropyrano[3,2-b]pyridine (3.2 g, 14.16 mmol) in DMF (20 ml) were added to the above solution and stirred overnight. EtOAc and water were added to the reaction mixture. The aqueous phase was extracted with EtOAc for 3 times, the combined organic phase was washed with water for 3 times, dried over Na2SO4, and concentrated in vacuum. The crude product was purified by silica gel chromatography (petroleum/EtOAc=1/1) to get the title compound as red solid.

Aufarbeitung

  1. extractionThe aqueous phase was extracted with EtOAc for 3 times
  2. washthe combined organic phase was washed with water for 3 times
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuum
  5. customThe crude product was purified by silica gel chromatography (petroleum/EtOAc=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-52828185a0c74abb8826b4998badf38e
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403845B2

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