Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isopropanol | HCID 3776 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 10827460 | HCID 10827460 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Product | HCID 67085866 | HCID 67085866 | — |
Reaction Steps
A mixture of benzyl 5-bromopicolinate (2.92 g, 10 mmol), potassium isopropenyl trifluoroborate (3.05 g, 21 mmol), Pd(dppf)Cl2 (445 mg, 0.54 mmol), and Et3N (1.4 mL) in isopropyl alcohol (20 mL) was degassed with N2 and heated at 80° C. for 7 h. The mixture was cooled to room temperature and diluted with EtOAc. The organic layer was washed with H2O, 5% citric acid, sat. NaHCO3 (aq.) and brine, then dried (MgSO4) and concentrated. The product benzyl 5-isopropenylpicolinate (1.27 g) was obtained by silica gel chromatography (elution with 0-16% EtOAc/Hex).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08729071B2 |
|---|
| Source dataset | uspto-grants-2014_05 |
|---|
| ORD ID | ord-918fce56c6ee4fac83a100442ef48cfe |
|---|
| Source note | uspto-grants-2014_05 |
|---|
