HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilylacetylene → 4-[(Trimethylsilyl)ethynyl]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-Bromopyridinium chloride | HCID 88100 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-[(Trimethylsilyl)ethynyl]pyridine | HCID 10773600 | — |
Reaction Steps
Heat a mixture of 4-bromopyridine hydrochloride (1.0 eq), ethynyl-trimethyl-silane (2.0 eq), PdCl2(PPh3)2 (0.1 eq), CuI (0.2 eq) and diisopropyl ethyl amine (10 eq) in DMF at 70° C. for 18 hours. Dilute with methylene chloride, and wash with water. Dry over MgSO4, filter and concentrate in vacuo. Purify the residue by flash chromatography on silica gel to give the title compound. MS (IS) 176.0 (M+1); TLC (20% ether in hexanes): Rf=0.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07320994B2 |
| Source dataset | uspto-grants-2008_01 |
| ORD ID | ord-32ee18b5a32b49b586301394c3e18a96 |
| Source note | uspto-grants-2008_01 |