Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | HCID 86692071 | HCID 86692071 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 67466257 | HCID 67466257 | 64.4% |
Reaction Steps
(S)-(6-Bromopyridin-2-yl)(3-(2-(trifluoromethyl)phenyl)pyrrolidin-1-yl)methanone (60 mg, 0.150 mmol), piperidine (15 mg, 0.180 mmol), Pd2(dba)3 (3 mg, 0.003 mmol), xantphos (5 mg, 0.009 mmol), and sodium-tert-butoxide (22 mg, 0.225 mmol) were suspended in toluene (3 ml), and then stirred at 100° C. under nitrogen stream for 3 hours. A saturated aqueous ammonium chloride solution (15 ml) was added to the resulting reaction liquid, followed by extraction with MC (15 ml×2). The organic layer was dried over anhydrous magnesium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (50% EtOAc/Hexanes), to obtain 39 mg of pale yellow oil (64%). MS (ESI): 404 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09096571B2 |
|---|
| Source dataset | uspto-grants-2015_08 |
|---|
| ORD ID | ord-af984e7e1bed4bee954c69ac5fc70182 |
|---|
| Source note | uspto-grants-2015_08 |
|---|
