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Stannane, tributyl(1-ethoxyethenyl)- → 1-(3-(Quinolin-6-ylmethyl)imidazo[1,2-a]pyrimidin-6-yl)ethanone

HRID 1892316
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1892316
Br[C:2]1[CH:3]=[N:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)=[CH:9][N:10]=2)[CH:7]=1.BrC1C=NC2N(C=C(CC3C=C4C(=CC=3)N=CC=C4)N=2)C=1.C([Sn](CCCC)(CCCC)[C:48]([O:50]CC)=[CH2:49])CCC>O1CCOCC1.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:18]1[C:19]2[C:14](=[CH:13][C:12]([CH2:11][C:8]3[N:6]4[CH:7]=[C:2]([C:48](=[O:50])[CH3:49])[CH:3]=[N:4][C:5]4=[N:10][CH:9]=3)=[CH:21][CH:20]=2)[CH:15]=[CH:16][CH:17]=1
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Komponenten

7

Edukt 3

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 581904746-((6-Bromoimidazo[1,2-a]pyrimidin-3-yl)methyl)quinolineHCID 669271896-(6-Bromo-imidazo[1,2-a]pyrimidin-2-ylmethyl)quinoline

Produkt 1

HCID 581904831-(3-(Quinolin-6-ylmethyl)imidazo[1,2-a]pyrimidin-6-yl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 8857Ethyl AcetateLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 6((6-bromoimidazo[1,2-a]pyrimidin-3-yl)methyl)quinoline and 6-(6-bromo-imidazo[1,2-a]pyrimidin-2-ylmethyl)quinoline (mixture, 250 mg, 0.737 mmol), PdCl2(PPh3)2 (51.7 mg, 0.074 mmol) and tributyl(1-ethoxyvinyl)stannane (399 mg, 1.106 mmol) in 5 mL of 1,4-dioxane was heated at 80° C. for 12 h under N2. The reaction mixture was diluted with EtOAc, washed with water. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was dissolved in HOAc and 3 N HCl and stirred at room temperature for 3 hours. The solvent was removed under reduced pressure and the residue was dissolved in CH2Cl2, washed with sat. aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography in silica gel eluting with a EtOAc/MeOH gradient to afford the title compound as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ ppm 8.97 (d, 1H), 8.84 (d, 1H), 8.67 (d, 1H), 8.04-7.99 (m, 2H), 7.74 (s, 1H), 7.53-7.51 (m, 1H), 7.34 (dd, 1H), 7.19 (s, 1H), 4.44 (s, 2H), 2.49 (s, 3H).

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in HOAc
  6. customThe solvent was removed under reduced pressure
  7. dissolutionthe residue was dissolved in CH2Cl2
  8. washwashed with sat. aqueous NaHCO3 and brine
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by flash chromatography in silica gel eluting with a EtOAc/MeOH gradient

Quellen und Nachweise

ORD-Eintrag
ord-8748beb4dbdc4cb095b3a3536884fb6a
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08507676B2

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