Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Fluorobenzamide | HCID 71572 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 86706558 | HCID 86706558 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86706557 | HCID 86706557 | — |
Reaction Steps
A suspension of 1-(2-chloro-pyridin-4-ylmethyl)-piperidine-4-carboxylic acid cyclohexylamide (50 mg, 0.15 mol), 4-fluoro-benzamide (20 mg, 0.15 mmol) and Cs2CO3 (5 mg, 0.16 mmol) in degassed dioxane (3 mL) is treated with 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (17 mg, 0.030 mmol) and tris(dibenzylideneacetone)dipalladium(0) (6.8 mg, 0.007 mmol). The reaction mixture is heated overnight at 100° C. The mixture is filtered, evaporated, dissolved in MeCN (1 mL) and purified by prep HPLC E. The product is dissolved in 2 ml HCl 1.25 N in MeOH and re-evaporated at HV, delivering the title compound hydrochloride as a slightly yellow powder, LC-MS A: tR=0.67 min; [M+H]+=439.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09428456B2 |
|---|
| Source dataset | uspto-grants-2016_08 |
|---|
| ORD ID | ord-0a59ee650b4f4f46b9319c72796a62c2 |
|---|
| Source note | uspto-grants-2016_08 |
|---|
