HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Ethynylpyridine → 4-Chloro-2-fluoro-6-pyridin-3-ylethynyl-phenylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Ethynylpyridine | HCID 186003 | — |
| Reactant | 4-Chloro-2-fluoro-6-iodoaniline | HCID 2773650 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 4-Chloro-2-fluoro-6-pyridin-3-ylethynyl-phenylamine | HCID 58215598 | — |
Reaction Steps
To a mixture of 3-ethynylpyridine (1.13 g, 11 mmol) and 2-fluoro-4-chloro-6-iodoaniline (2.71 g, 10 mmol) in triethylamine (100 mL) is added PdCl2(PPh3)2 (175 mg, 0.25 mmol) and CuI (95 mg, 0.50 mmol) and the mixture is refluxed for 1 h. The solvent is removed in vacuo and the residue is purified by silica gel flash chromatography (dichloromethane-methanol, 1:0 to 24:1) to give 4-chloro-2-fluoro-6-pyridin-3-ylethynyl-phenylamine. MS (ESI) m/z 247 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09242963B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-dc15832643bd49ac96a2a1f259f4d5b0 |
| Source note | uspto-grants-2016_01 |