HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 69084239, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Iodoanisole | HCID 69676 | — |
| Reactant | HCID 86626641 | HCID 86626641 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1) | HCID 11029508 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69084239 | HCID 69084239 | 48.3% |
Reaction Steps
Tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (64 mg, 0.03 eq.), 4-iodoanisole (531 mg, 1.1 eq.), triethylamine (862 μL, 3.0 eq.), and copper (I) iodide (23.6 mg, 0.06 eq.) were added sequentially to a solution of 2-ethyl-1-(2-propynyl)-1H-imidazo[4,5-c]quinoline (485 mg, 2.06 mmol, 1.0 eq.) in DMF (10 mL). The reaction mixture was stirred at ambient temperature for 3 hour and then concentrated under reduced pressure. The residue was purified by column chromatography (silica gel eluting with 2/98 methanol/chloroform) to provide 0.34 g of 2-ethyl-1-[3-(4-methoxyphenyl)-2-propynyl]-1H-imidazo[4,5-c]quinoline as a clear oil that partially crystallized on standing.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08802853B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-11d66dd5e5934181a89899603d3324d4 |
| Source note | uspto-grants-2014_08 |