HuagongsheHuagongshe Chemistry Print Report · For research reference only
Binap, (A+-)- → HCID 86645834, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 2-Bromo-5-(trifluoromethyl)pyridine | HCID 2736434 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate | HCID 34178604 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 86645834 | HCID 86645834 | 40% |
Reaction Steps
A mixture of tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (2.5 mmol, 1.0 eq.) and 2-bromo-5-(trifluoromethyl)pyridine (2.5 mmol, 1.0 eq.) and tBuONa (7.5 mmol, 3.0 eq.) in toluene (12 ml) was degassed with argon for 10 min. BINAP (0.15 mmol, 0.06 eq.) and Pd(OAc)2 (0.05 mmol, 0.02 eq.) were added and the reaction mixture obtained was heated under reflux for 14 h. The reaction mixture was filtered over Celite and the filtrate was concentrated in vacuo in order to obtain the crude product, which was purified by column chromatography (silica gel, 22-25% ethyl acetate in hexane), in order to obtain the desired product. Yield: 40%
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08455475B2 |
| Source dataset | uspto-grants-2013_06 |
| ORD ID | ord-e07fd31bb4484ffa8d91bb9c2ac6b782 |
| Source note | uspto-grants-2013_06 |