Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2734771 | — |
| Reactant | [2-(4-Bromo-phenyl)ethyl]-carbamic acid tert-butyl ester | HCID 14221818 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethylacetate heptane | HCID 21899848 | — |
| Product | HCID 71150146 | HCID 71150146 | 95% |
Reaction Steps
IMS (50 mL) and water (16 mL) were degassed thoroughly. tert-Butyl 4-bromophenethylcarbamate (3.52 g, 11.7 mmol), sodium carbonate (5.0 g, 46.9 mmol), palladium tetrakis (1.35 g, 1.2 mmol) and 1-benzyl-1H-pyrazole-4-boronic acid pinacol ester (5.0 g, 17.6 mmol) were added and the reaction mixture heated to 90° C. overnight. The reaction was partitioned between ethyl acetate (500 mL) and water (250 mL) and brine (250 mL), then dried (MgSO4). Filtration and removal of the solvent gave the crude residue which was subject to column chromatography (50% ethyl acetate/heptane) to give tert-butyl 4-(6-oxo-1,6-dihydropyridin-3-yl)phenethylcarbamate (4.2 g, 11.1 mmol, 95% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09415045B2 |
|---|
| Source dataset | uspto-grants-2016_08 |
|---|
| ORD ID | ord-842365a2e2b34366bed03cb1352bf6a1 |
|---|
| Source note | uspto-grants-2016_08 |
|---|
