Acetonitrile → HCID 18760204, compound

HRID 432682Notes

Reaction equation

HRID 432682 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:9]=[CH:8]1)#[C:2][CH3:3].C(N(CC)CC)C.C(#N)C.I[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[OH:37]>ClCCl.[Cu]I.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.CO>[O:37]1[C:2]([CH2:1][O:4][CH2:5][CH2:6][N:7]2[C:19]3[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[N:12]=[CH:11][C:10]=3[N:9]=[CH:8]2)=[CH:3][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]1=2

Participants

9

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 107842-IodophenolHCID 18760203HCID 18760203, compound

Product 1

HCID 18760204HCID 18760204, compoundYield 62.9%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Under a nitrogen atmosphere, 1-[2-(propynyloxy)ethyl]-1H-imidazo[4,5-c]quinoline (1.0 g, 4.21 mmol), triethylamine (1.53 mL, 10.96 mmol) and anhydrous acetonitrile (20 mL) were combined and then heated to 60° C. 2-Iodophenol (1.02 g, 4.63 mmol), copper (I) iodide (0.08 g) and dichlorobis(triphenylphosphine)palladium(II) (0.148 g) were added. After 4 hours analysis by TLC (5% methanol in dichloromethane) indicated that the reaction was complete. The reaction mixture was filtered through a layer of Celite® filter aid to remove the catalysts. The filtrate was concentrated under reduced pressure to provide an oil. This material was purified by flash chromatography (silica gel eluting with 3% methanol in dichloromethane) to provide 0.91 g of 1-[2-(benzo[b]furan-2-ylmethoxy)ethyl]-1H-imidazo[4,5-c]quinoline as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through a layer of Celite®
  2. filtrationfilter aid
  3. customto remove the catalysts
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto provide an oil
  6. customThis material was purified by flash chromatography (silica gel eluting with 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-85779003b5b84429a25e9cf771e362fe
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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