Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | tert-Butyl carbamate | HCID 77922 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 90426423 | HCID 90426423 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 131733477 | HCID 131733477 | 113% |
Reaction Steps
A mixture of Example C8 (1 g, 2.131 mmol), t-butyl carbamate (0.749 g, 6.39 mmol), Cs2CO3 (2.083 g, 6.39 mmol) and Xantphos (0.555 g, 0.959 mmol) in dioxane (15 mL) was sparged with Ar, treated with Pd2(dba)3 (0.293 g, 0.320 mmol), sparged again with Ar and heated at 100° C. overnight. The mixture was cooled to RT, treated with satd. NaHCO3, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4, passed through a pad of silica gel and concentrated to dryness to afford crude tert-butyl (4-(2-chloro-5-fluoro-4-(2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamido)phenoxy)pyridin-2-yl)carbamate (1.32 g, 113%) which was used without further purification. MS (ESI) m/z: (M+H+): 550.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09133183B2 |
|---|
| Source dataset | uspto-grants-2015_09 |
|---|
| ORD ID | ord-7d612de34b7745b0ab3199e858b0faca |
|---|
| Source note | uspto-grants-2015_09 |
|---|
