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

HRID 1872922

Reaktionsgleichung

Reaktionsgleichung von HRID 1872922
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]-ethanol

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.

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-abdb49f8720e4c74b8bc1f29367a264b
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06110931

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