HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1255916Generated: November 2, 2026
Trimethylsilylacetylene → 3-(Pyrrolidin-1-ylmethyl)-5-[(trimethylsilyl)ethynyl]pyridine
https://huagongshe.com/reaction/1255916
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3-Bromo-5-(pyrrolidin-1-ylmethyl)pyridine | HCID 21255945 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-(Pyrrolidin-1-ylmethyl)-5-[(trimethylsilyl)ethynyl]pyridine | HCID 21255932 | — |
Reaction Steps
A mixture of 3-bromo-5-(pyrrolidin-1-ylmethyl)pyridine (0.76 mmol), ethynyltrimethylsilane (0.91 mmol), Pd(PPh3)4 (0.038 mmol), CuI (0.076 mmol), and 0.26 mL (1.52 mmol) of diisopropylethylamine in 3.8 mL of DMF can be heated at 50° C. overnight under an atmosphere of N2. Upon cooling to ambient temperature, the reaction mixture is concentrated and the crude product is purified by silica gel flash chromatography (eluted with 50% EtOAc/hexanes).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08461167B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-1c399858d05c49b3bda92158e3a477b2 |
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| Source note | uspto-grants-2013_06 |
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