Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Iodophenol | HCID 10784 | — |
| Reactant | HCID 18760203 | HCID 18760203 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 18760204 | HCID 18760204 | 62.9% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06664260B2 |
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| Source dataset | uspto-grants-2003_12 |
|---|
| ORD ID | ord-85779003b5b84429a25e9cf771e362fe |
|---|
| Source note | uspto-grants-2003_12 |
|---|
