Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetamide | HCID 178 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 89827736 | HCID 89827736 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 89827691 | HCID 89827691 | 90% |
Reaction Steps
Sparge a mixture of tert-butyl (5-(7-chloro-2-methyl-1,6-naphthyridin-3-yl)-2,4-difluorophenyl)carbamate (0.664 g, 1.636 mmol), XantPhos (0.189 g, 0.327 mmol), Cs2CO3 (1.066 g, 3.27 mmol) and acetamide (0.483 g, 8.18 mmol) in dioxane (16 mL) with Ar, add Pd2(dba)3 (0.150 g, 0.164 mmol) and heat at 100° C. overnight. Cool to RT, remove the solids via filtration through diatomaceous earth, rinse well with THF, concentrate the filtrate to dryness and purify via silica gel chromatography (EtOAc/Hex) to afford the title compound (630 mg, 90%) as a glass. MS (ESI) m/z: 429.2 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09187474B2 |
|---|
| Source dataset | uspto-grants-2015_11 |
|---|
| ORD ID | ord-8c6720f76bea4b02bdb75b9c34e9e307 |
|---|
| Source note | uspto-grants-2015_11 |
|---|
