HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 6-(4-Chloro-phenyl)-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-quinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Bromo-6-(4-chloro-phenyl)-quinoline | HCID 85969692 | — |
| Reactant | 1-[2-(4-Ethynyl-phenoxy)-ethyl]-pyrrolidine | HCID 85969815 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 6-(4-Chloro-phenyl)-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-quinoline | HCID 59835838 | — |
Reaction Steps
In a nitrogen atmosphere, 0.6 mg CuI, 9.3 mg Pd(PPh3)2Cl2 and 318 mg (1 mmol) 2-bromo-6-(4-chloro-phenyl)-quinoline are added successively to a solution of 142 mg (0.66 mmol) 1-[2-(4-ethynyl-phenoxy)-ethyl]-pyrrolidine and 2.6 mL (18.67 mmol) triethylamine in 5 mL absolute DMF and 10 mL acetonitrile. The reaction mixture is stirred for 14 h at RT and evaporated down. The purification is carried out by column chromatography on silica gel (DCM/MeOH/NH3 90:10:1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08618132B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-edafc43fbf92438a81c863e1df397e43 |
| Source note | uspto-grants-2013_12 |