Dimethylformamide → 2-[3-(2-Trimethylsilylethoxymethyl)-3H-imidazo[4,5-b]pyridin-6-yl]-ethanol

HRID 377223

Reaktionsgleichung

Reaktionsgleichung von HRID 377223
Br[C:2]1[CH:3]=[C:4]2[N:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=1.C(C([Sn])=C(CC[CH2:31][CH3:32])CCCC)CCC.CN(C=[O:38])C>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:16][Si:15]([CH3:18])([CH3:17])[CH2:14][CH2:13][O:12][CH2:11][N:8]1[C:5]2=[N:6][CH:7]=[C:2]([CH2:32][CH2:31][OH:38])[CH:3]=[C:4]2[N:10]=[CH:9]1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 193582886-Bromo-3-[[2-(trimethylsilyl)ethoxy]methyl]-3H-imidazo[4,5-b]pyridineHCID 53438229Tri(butyl)vinyltin

Produkt 1

HCID 186871442-[3-(2-Trimethylsilylethoxymethyl)-3H-imidazo[4,5-b]pyridin-6-yl]-ethanolAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysator

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a solution of 6-bromo-3-(2-trimethysilylethoxymethyl)-3H-imidazo-[4,5-b]-pyridine (1.3 g, 4 mmol) and bis(triphenylphosphine)-palladium (II) chloride in DMF (12 mL) was added tributylvinyl tin (2.14 g, 6.7 mmol). The reaction vessel was evacuated-purged (N2) several times followed by heating to 95° C. for 15 h. After cooling, the crude reaction mixture was filtered through a pad of celite® and eluted with ethyl ether. The ethereal mixture was washed several times with saturated KF, brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel using a gradient elution of ethyl acetate/hexanes (10, 20, 30 to 40%) which provided 1.06 g of the title compound (97% yield).

Aufarbeitung

  1. customThe reaction vessel was evacuated-purged (N2) several times
  2. temperatureAfter cooling
  3. customthe crude reaction mixture
  4. filtrationwas filtered through a pad of celite®
  5. washeluted with ethyl ether
  6. washThe ethereal mixture was washed several times with saturated KF, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified by flash chromatography on silica gel using
  11. washa gradient elution of ethyl acetate/hexanes (10, 20, 30 to 40%) which

Quellen und Nachweise

ORD-Eintrag
ord-121b124c3ba44a82ab92077c1e1cdfa5
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06025366

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