Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Bromo-1-fluoro-2-iodobenzene | HCID 2782750 | — |
| Reactant | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Reactant | 4-(Aminosulphonyl)benzeneboronic acid | HCID 22391977 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86723228 | HCID 86723228 | 55% |
Reaction Steps
To 4-bromo-1-fluoro-2-iodobenzene (361 mg, 1.2 mmol) and 4-sulfamoyl-phenylboronic acid (240 mg, 1.20 mmol) in 4:1 dioxane/H2O (5 mL) was added Na2CO3 (382 mg, 3.60 mmol) and [1,1′-Bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (34.3 mg, 0.042 mmol). The reaction was heated under microwave irradiation at 120° C. for 15 minutes, cooled and diluted with EtOAc and water. The aqueous layer was extracted with EtOAc and the combined organic layers dried over Na2SO4. The solvent was removed in vacuo and the resulting residue purified via silica gel column chromatography eluting with EtOAc:heptanes 0:1 to 1:1 to afford the desired product 55%, 218 mg, 55%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08952008B2 |
|---|
| Source dataset | uspto-grants-2015_02 |
|---|
| ORD ID | ord-548cb92f46994c4a9aa5a5f988ec693a |
|---|
| Source note | uspto-grants-2015_02 |
|---|
