Potassium Carbonate → 4-Methylene-6-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-2,3-dihydropyrano[3,2-b]pyridine

HRID 2279271Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2279271
CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[K+].[K+].[CH3:49][C:50]1[N:51]=[C:52]([C:55]2[CH:56]=[N:57][CH:58]=[CH:59][CH:60]=2)[S:53][CH:54]=1.Br[C:62]1[N:67]=[C:66]2[C:68](=[CH2:72])[CH2:69][CH2:70][O:71][C:65]2=[CH:64][CH:63]=1>C(OCC)(=O)C.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:72]=[C:68]1[C:66]2=[N:67][C:62]([C:54]3[S:53][C:52]([C:55]4[CH:56]=[N:57][CH:58]=[CH:59][CH:60]=4)=[N:51][C:50]=3[CH3:49])=[CH:63][CH:64]=[C:65]2[O:71][CH2:70][CH2:69]1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 12015543-(4-Methyl-1,3-thiazol-2-yl)pyridineHCID 584840716-bromo-4-methylene-3,4-dihydro-2H-pyrano[3,2-b]pyridine

Produkt 1

HCID 1317334814-Methylene-6-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-2,3-dihydropyrano[3,2-b]pyridineAusbeute 22,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a stirred mixture of Pd2(dba)3 (270 mg, 0.3 mmol), xantphos (870 mg, 1.5 mmol), K2CO3 (1.52 g, 11 mmol) and 3-(4-methylthiazol-2-yl)pyridine (1.76 g, 10 mmol) in a sealed tube was added 6-bromo-4-methylene-2,3-dihydropyrano[3,2-b]pyridine (2.49 g, 11 mmol) in 1,4-dioxance (30 mL). The mixture was stirred at 120° C. for 18 hours. The mixture was diluted with Ethyl acetate and H2O, the organic layer was washed with brine and water, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by silica gel chromatography (petroleum/Ethyl acetate=3/1) to give the title compound as red solid (710 mg, 22%). 1H NMR (400 Mz, DMSO-d6): δ: 2.69 (s, 3H); 2.81 (t, J=6, 2H); 4.25 (t, J=5.1, 2H); 5.16 (s, 1H); 6.16 (s, 1H); 7.38 (d, J=8.7, 1H); 7.55-7.50 (m, 1H); 7.6 (d, J=8.7, 1H); 8.31-8.27 (m, 1H); 8.66-8.64 (m, 1H); 9.12 (s, 1H).

Aufarbeitung

  1. washthe organic layer was washed with brine and water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by silica gel chromatography (petroleum/Ethyl acetate=3/1)

Quellen und Nachweise

ORD-Eintrag
ord-50730b6847e4486a9d9e2adb71b172e4
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133218B2

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