HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → HCID 71212808, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 5-Bromoindole | HCID 24905 | — |
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate | HCID 16217654 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 71212808 | HCID 71212808 | — |
Reaction Steps
To a degassed solution of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (138 mg, 0.47 mmol), 5-bromo-indole (63 mg, 0.24 mmol), CsF (107 mg, 0.71 mmol), and X-Phos (11.2 mg, 0.023 mmol) in dioxane (2 mL) was added palladium acetate (2.6 mg, 0.012 mmol) under nitrogen. The mixture was then heated to 90 C overnight, cooled to r.t., and diluted with EtOAc. Following filtration and concentration in vacuo, the residue was purified on silica (0-30% EtOAc/hexanes) to yield the title product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09102673B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-cb0a3fb552174cea9fabdcf44e951fba |
| Source note | uspto-grants-2015_08 |