HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium fluoride → 2-(4-Chloro-6-(4-isopropoxyphenyl)pyridin-2-yl)pyrazine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 2-(Tributylstannyl)pyrazine | HCID 2737316 | — |
| Reactant | 2,4-Dichloro-6-(4-isopropoxyphenyl)pyridine | HCID 90118079 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Product | 2-(4-Chloro-6-(4-isopropoxyphenyl)pyridin-2-yl)pyrazine | HCID 90118285 | 64% |
Reaction Steps
To a 2 dram vial equipped with a stir bar was added 2,4-dichloro-6-(4-isopropoxyphenyl)pyridine (50 mg, 0.18 mmol), 2-(tributylstannyl)pyrazine (65 mg, 0.18 mmol), CuI (9.0 mg, 0.047 mmol), CsF (82 mg, 0.54 mmol), and Pd(PPh3)4 (10.2 mg, 8.86 μmol). The vial was capped with a septum screw-cap and then placed under N2 atmosphere. To the vial was added degassed DMF (1 mL). The vial was placed in a 80° C. heating block with stirring for 1 hour. The reaction mixture was directly purified by C18 chromatography (water:MeOH w/0.1% TFA) to afford 2-(4-chloro-6-(4-isopropoxyphenyl)pyridin-2-yl)pyrazine as a dark solid (37 mg, 64%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09334279B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-71c5379fc1e0476e842fe6f6a6054db7 |
| Source note | uspto-grants-2016_05 |