Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 9-Borabicyclo(3.3.1)nonane | HCID 78966 | — |
| Reactant | 5-Bromo-2,2-difluoro-1,3-benzodioxole | HCID 2736271 | — |
| Reactant | tert-Butyl 3-ethenylpyrrolidine-1-carboxylate | HCID 53302213 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | N,N-Dimethylformamide--water (1/1) | HCID 21962138 | — |
| Product | HCID 66974058 | HCID 66974058 | 98% |
Reaction Steps
A stream of N2 was bubbled through neat 3-vinyl-pyrrolidine-1-carboxylic acid tert-butyl ester (589 mg, 2.99 mmol) for 15 min before adding 9-BBN (0.5 M in THF, 6 mL). The reaction mixture was heated at reflux for 2 h, then cooled to rt. The reaction mixture was then added, via cannula, to a preformed solution consisting of 5-bromo-2,2-difluoro-1,3-benzodioxole (704 mg, 2.97 mmol), Pd(dppf)Cl2.CH2Cl2 (69.7 mg, 0.0953 mmol), and potassium carbonate (559 mg, 4.04 mmol) in DMF/H2O (10 mL/1 mL). The resultant mixture was heated at 60° C. for 18 h, cooled to rt, and poured into water. The pH of the mixture was adjusted to 11 with NaOH (1 N) and extracted with EtOAc (3×). The organic layers were combined, dried (Na2SO4), and concentrated. The crude residue was purified (FCC) to give the title compound (1.0 g, 98%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08901111B2 |
|---|
| Source dataset | uspto-grants-2014_12 |
|---|
| ORD ID | ord-c2af606677024e008e8fb05d402e9b3b |
|---|
| Source note | uspto-grants-2014_12 |
|---|
