HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilylacetylene → HCID 69349409, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-((6-Iodopyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one | HCID 86229368 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69349409 | HCID 69349409 | 93.3% |
Reaction Steps
According to Scheme 33 Step 2: A mixture of 1-((6-iodopyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (0.48 mmol, 200 mg), PdCl2(PPh3)2 (33 μmol, 23 mg), CuI (24 μmol, 4.5 mg), iPr2EtN (0.99 mmol, 1.72 μl), trimethylsilylacetylene (1.43 mmol, 203 μL) and DMF (3 mL, previously deoxygenated) was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure. The residue was purified in a manifold (vac.) using a Sep-Pak silica cartridge CH2Cl2/MeOH(NH3)sat. 3% yielding 5-(4-methoxyphenyl)-1-((6-(2-(trimethylsilyl)ethynyl)pyridin-3-yl)methyl)pyridin-2(1H)-one (174 mg, 93%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08399493B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-9fd1087fd58947469aeda82205facf51 |
| Source note | uspto-grants-2013_03 |