Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Bromopyridinium chloride | HCID 88100 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 66799345 | HCID 66799345 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 66798737 | HCID 66798737 | 41% |
Reaction Steps
Benzyl methyl(2-oxopiperidin-4-yl)carbamate (300 mg, 1.145 mmol, 1.0 eq.), 4-bromopyridine HCl (244 mg, 1.259 mmol, 1.1 eq.) and Cs2CO3 (744 mg, 2.29 mmol, 2.0 eq.) were taken up in toluene and degassed with N2. Xantphos (66 mg, 0.114 mmol, 0.1 eq.) and Pd2(dba)3 (104 mg, 0.114 mmol, 0.1 eq.) were then added and the mixture was heated for 14 hours at 90° C. After monitoring by TLC, the reaction mixture was filtered over Celite and the filtrate was concentrated under reduced pressure and purified by column chromatography (Alox, 1% MeOH in DCM). Yield: 41% (160 mg, 0.472 mmol)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08680159B2 |
|---|
| Source dataset | uspto-grants-2014_03 |
|---|
| ORD ID | ord-6afc62039e4c4f12bf9b0e04fcc15402 |
|---|
| Source note | uspto-grants-2014_03 |
|---|
