HuagongsheHuagongshe Chemistry Print Report · For research reference only
Piperidine → Ethyl 1-(3-(naphthalen-1-yloxy)propyl)-3-(piperidin-1-yl)-1h-indole-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | Ethyl 3-bromo-1-(3-(naphthalen-1-yloxy)propyl)-1h-indole-2-carboxylate | HCID 67316935 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Ethyl 1-(3-(naphthalen-1-yloxy)propyl)-3-(piperidin-1-yl)-1h-indole-2-carboxylate | HCID 67316989 | — |
Reaction Steps
A mixture of EXAMPLE 31C (100 mg), piperidine (57 mg), tris(dibenzylideneacetone)dipalladium(0) (20 mg), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (26 mg) and Cs2CO3 (216 mg) in toluene (2 mL) was heated at 100° C. for 48 hours. The mixture was diluted with ethyl acetate and was washed with water and brine. The organic phase was dried (Na2SO4) filtered, and concentrated. The concentrate was purified by flash chromatography on silica gel with 0-10% ethyl acetate/hexanes.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08853209B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-967cbbe7d3394feaae49e0da53e88c12 |
| Source note | uspto-grants-2014_10 |