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

HRID 1872922

반응식

HRID 1872922 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매

반응 조건

온도
95 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-abdb49f8720e4c74b8bc1f29367a264b
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06110931

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