HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 606850Generated: October 25, 2026
Triethylamine → 3-(5-Fluoropyridin-3-ylethynyl)-benzonitrile
https://huagongshe.com/reaction/606850
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonic acid, trifluoro-, 5-fluoro-3-pyridinyl ester | HCID 11413882 | — |
| Reactant | 3-Ethynylbenzonitrile | HCID 12088964 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178419050 | HCID 178419050 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-(5-Fluoropyridin-3-ylethynyl)-benzonitrile | HCID 67047857 | 35% |
Reaction Steps
Add triethylamine (0.79 mL, 5.64 mmol), copper (I) iodide (15.43 mg, 0.08 mmol) and bis(triphenylphosphine)palladium (II) dichloride (49.48 mg, 0.07 mmol) to a solution of trifluoromethanesulfonic acid 5-fluoropyridin-3-ylester, (prepared as described in PREPARATION 6), (345 mg, 1.41 mmol) and 3-ethynylbenzonitrile, prepared as described in PREPARATION 8), (230 mg, 1.41 mmol) in ethyl acetate (2 mL). Stir in a sealed tube at 70° C. for 18 h. Concentrate and purify by silica gel chromatography, eluting with 100:0 to 0:100 hexanes:ethyl acetate, to give the title compound (109 mg, 35%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07915424B2 |
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| Source dataset | uspto-grants-2011_03 |
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| ORD ID | ord-00e5dd7316bb4fc49f1332edc1ae2be3 |
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| Source note | uspto-grants-2011_03 |
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