HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1513649Generated: October 26, 2026
Trimethylsilylacetylene → 4-((6-Ethynyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline
https://huagongshe.com/reaction/1513649
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Tri-tert-butylphosphine tetrafluoroborate | HCID 2734635 | — |
| Reactant | 4-((6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline | HCID 57691027 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-((6-Ethynyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline | HCID 86630263 | — |
Reaction Steps
Step 1. Tri-t-butylphosphonium tetrafluoroborate (0.0377 g, 0.130 mmol), tris(dibenzylideneacetone)dipalladium (0.0594 g, 0.0649 mmol), trimethylsilyl acetylene (1.82 ml, 13.0 mmol), 4-((6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline (0.500 g, 1.30 mmol) were taken up in dioxane (10 mL) and triethylamine (3 mL). Added CuI. Sealed in a tube and heated at 80° C. for 3 h. Concentrated. Took up in MeOH and added solid potassium carbonate (large excess). Allowed to stir for 30 min. Filtered through a plug of Celite and concentrated. Took up in 10% MeOH in DCM and filtered through a plug of silica gel to afford 4-((6-ethynyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline. MS m/z=331.0[M+1]+. Calc'd for C19H14N4O2: 330.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08217177B2 |
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| Source dataset | uspto-grants-2012_07 |
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| ORD ID | ord-b6377f1829c543d68201cebab4002d00 |
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| Source note | uspto-grants-2012_07 |
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