HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 606892Generated: October 30, 2026
Triethylamine → 3-Chloro-5-(4-fluorophenylethynyl)-pyridine
https://huagongshe.com/reaction/606892
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 1-Ethynyl-4-fluorobenzene | HCID 522627 | — |
| Reactant | 5-Chloropyridin-3-yl trifluoromethanesulfonate | HCID 15185870 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178419050 | HCID 178419050 | — |
| Product | 3-Chloro-5-(4-fluorophenylethynyl)-pyridine | HCID 67047748 | 65% |
Reaction Steps
Add 4-fluorophenylacetylene (1.0 g, 8.35 mmol), triethylamine (4 mL, 30 mmol), copper (I) iodide (76 mg, 0.40 mmol), and bis(triphenylphosphine)palladium (II) dichloride (140 mg, 0.20 mmol) to a solution of trifluoromethanesulfonic acid 5-chloropyridin-3-yl ester, (prepared as described in PREPARATION 25) in ethyl acetate (1.95 g, 7.5 mmol), (7 mL) under nitrogen and heat at 60° C. for 12 h. Concentrate and purify the residue by silica gel chromatography, eluting with dichloromethane to give the title compound as a white solid (1.12 g, 65%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07915424B2 |
|---|
| Source dataset | uspto-grants-2011_03 |
|---|
| ORD ID | ord-c41f0e2fa3544935a1e62064869a8e4b |
|---|
| Source note | uspto-grants-2011_03 |
|---|
