Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | 2-Aminothiazole | HCID 2155 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2,6-Dichloropyridine | HCID 16989 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57562594 | HCID 57562594 | 63.3% |
Reaction Steps
A mixture of 1.37 g (9.26 mmol) of 2-aminothiazole, 0.74 g (7.39 mmol) of 2,6-dichloropyridine, 387 mg (0.621 mmol) of (S)-(−)-2,2′-(bisdiphenylphosphino)-1,1′-binaphthyl, 322 mg (0.311 mmol) of tris(dibenzylideneacetone)dipalladium(0)-chloroform complex, 2.77 g (8.50 mmol) of cesium carbonate and 10 ml of toluene was heated under reflux for 1 hour and 30 minutes, cooled to room temperature and diluted with ethyl acetate. An insoluble matter was filtered off using Celite and the resulting ethyl acetate solution was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated. The residue was purified by a silica gel column chromatography to give 990 mg (4.68 mmol) of the title compound as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07834018B2 |
|---|
| Source dataset | uspto-grants-2010_11 |
|---|
| ORD ID | ord-664342d1e05f4d81b4b4c4503b0c2144 |
|---|
| Source note | uspto-grants-2010_11 |
|---|