Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 3,5-Dibromopyridine | HCID 69369 | — |
| Reactant | HCID 178478979 | HCID 178478979 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Catalyst | Zincchloride | HCID 3007855 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Product | HCID 18187614 | HCID 18187614 | 33% |
Reaction Steps
A dry flask under nitrogen was charged with zinc chloride (16 mL, 0.5 M in THF, 8 mmol), and a solution of phenylmagnesium chloride (4 mL, 2.0 M in THF, 8 mmol). The mixture was heated to 50° C. for 3h then cooled to room temperature and transferred via cannula to a solution of 3,5-dibromopyridine (1.26 g, 5.3 mmol), copper iodide (61 mg, 0.32 mmol), and bis(diphenylphosphino)ferrocene palladium dichloride (218 mg, 0.27 mmol) in 15 mL THF. The resulting mixture was heated to 50° C. overnight. Sat′d ammonium chloride was added and the mixture was extracted with ethyl acetate. The organic portion was dried over sodium sulfate and concentrated. Flash chromatography (8/1 hexane/ethyl acetate) afforded 433 mg (33%) of the title compound. 1H NMR (400 MHz, CDCl3). δ 4.02 (s, 2H), 7.18-7.4 (m, 8H), 7.65 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06538002B1 |
|---|
| Source dataset | uspto-grants-2003_03 |
|---|
| ORD ID | ord-9766e341e2564b80ba7a7da373f1ca8b |
|---|
| Source note | uspto-grants-2003_03 |
|---|
