Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | 1-Bromo-4-iodobenzene | HCID 11522 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Ethyl 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxylate | HCID 53217182 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water 1,2-dimethoxyethane | HCID 18180031 | — |
| Solvent | Water ethylacetate | HCID 22728543 | — |
| Product | HCID 67957853 | HCID 67957853 | — |
Reaction Steps
1-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester (2 g, 6.33 mmol), 1-bromo-4-iodo-benzene (1.97 g, 6.96 mmol), and sodium bicarbonate (1.59 g, 18.98 mmol) were dissolved in DME:H2O (2:1). The solution was sparged with N2 (g) for ten minutes then (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.52 g, 0.063 mmol) was added and N2 (g) was introduced for an additional 5 minutes. The reaction was heated to 80° C. for 4 hours then cooled and submitted to EtOAc/H2O workup. The crude material was purified on silica gel (0-70% EtOAc in hexanes) to provide the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09272990B2 |
|---|
| Source dataset | uspto-grants-2016_03 |
|---|
| ORD ID | ord-84cd09d306504cef91e8be2367c8fff4 |
|---|
| Source note | uspto-grants-2016_03 |
|---|
