HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1054946Generated: October 26, 2026
Triethylamine → 1-(4-methoxy-benzyl)-5-pyrrolidin-1-yl-3-trimethylsilanylethynyl-1H-[1,2,4]triazole
https://huagongshe.com/reaction/1054946
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 3-bromo-1-(4-methoxy-benzyl)-5-pyrrolidin-1-yl-1H-[1,2,4]triazole | HCID 90016950 | — |
| Catalyst | Triphenylphosphine | HCID 11776 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-(4-methoxy-benzyl)-5-pyrrolidin-1-yl-3-trimethylsilanylethynyl-1H-[1,2,4]triazole | HCID 90016562 | 45.9% |
Reaction Steps
A mixture of 3-bromo-1-(4-methoxybenzyl)-5-(pyrrolidin-1-yl)-1H-1,2,4-triazole (197 mg, 584 μmol, Eq: 1.00), ethynyltrimethylsilane (115 mg, 164 μl, 1.17 mmol, Eq: 2) and triethylamine (88.7 mg, 122 μl, 876 μmol, Eq: 1.5) in tetrahydrofuran (3 ml) was purged for 5 minutes with nitrogen. Then copper (I) iodide (1.11 mg, 5.84 μmol, Eq: 0.01), bis(triphenylphosphine) palladium(II) chloride (4.1 mg, 5.84 μmol, Eq: 0.01) and triphenylphosphine (1.53 mg, 5.84 μmol, Eq: 0.01) were added, the vessel was capped and heated to 75° C. for 18 hours. The crude material was applied on silicagel and purified by flash chromatography over a 20 g silicagel column using heptane/ethyl acetate 10-30% as eluent affording 1-(4-methoxy-benzyl)-5-pyrrolidin-1-yl-3-trimethylsilanylethynyl-1H-[1,2,4]triazole (95 mg/45.9%) as an orange oil. MS: m/e=355.4 (M+H+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09394311B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-140f27199723490e9e77c6eee6537d5f |
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| Source note | uspto-grants-2016_07 |
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