HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-(5-Methylsulfanylpyridin-3-ylethynyl)-benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Ethynylbenzonitrile | HCID 12088964 | — |
| Reactant | 3-Bromo-5-(methylthio)pyridine | HCID 22390359 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178419050 | HCID 178419050 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-(5-Methylsulfanylpyridin-3-ylethynyl)-benzonitrile | HCID 67047738 | 41% |
Reaction Steps
Add copper (I) iodide (20.0 mg, 0.18 mmol), bis(triphenylphosphine)palladium (II) dichloride (64.2 m g, 0.092 mmol) and triethylamine (1.03 mL, 7.32 mmol), to a solution of 3-bromo-5-methylsulfanylpyridine, (prepared as described in PREPARATION 29), (375 mg, 1.83 mmol) and 3-ethynylbenzonitrile, (prepared as described in PREPARATION 8), (465 mg, 3.66 mmol) in ethyl acetate (3 mL) and stir at 90° C. overnight. Cool to room temperature, concentrate and purify the residue by silica gel chromatography, eluting with hexanes/ethyl acetate, to give the title compound (187 mg, 41%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07915424B2 |
| Source dataset | uspto-grants-2011_03 |
| ORD ID | ord-5375a83d112241129b1abe61742c4c3d |
| Source note | uspto-grants-2011_03 |