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

HRID 377223

Reaction equation

HRID 377223 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
95 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-121b124c3ba44a82ab92077c1e1cdfa5
Source dataset
uspto-grants-2000_02
Patent number
US06025366

Linked notes

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