HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-Chloro-5-(4-fluoro-3-methoxyphenylethynyl)-pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Chloro-5-ethynylpyridine | HCID 23500887 | — |
| Reactant | 1-Fluoro-4-iodo-2-methoxybenzene | HCID 26598241 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178419050 | HCID 178419050 | — |
| Product | 3-Chloro-5-(4-fluoro-3-methoxyphenylethynyl)-pyridine | HCID 67047781 | 95.5% |
Reaction Steps
Dissolve 1-fluoro-4-iodo-2-methoxybenzene, (prepared as described in PREPARATION 47), (480 mg, 1.9 mmol) in triethylamine (7 mL, 53 mmol) and add 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (250 mg, 1.8 mmol) followed by bis(triphenylphosphine)palladium (II) dichloride (51 mg, 0.07 mmol) and copper (I) iodide (28 mg, 0.15 mmol). Stir for 18 h at room temperature, concentrate, and purify by silica gel chromatography, eluting with 3:1 hexanes:ethyl acetate. Further purify on silica gel, eluting with 100% dichloromethane, to give the title compound as a white solid (450 mg, 94%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07915424B2 |
| Source dataset | uspto-grants-2011_03 |
| ORD ID | ord-609cc0c1b0a94dc48f8e0b644ad8ba5c |
| Source note | uspto-grants-2011_03 |