Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Sodium Sulfate | HCID 24436 | — |
| Reactant | 4-Bromo-1-fluoro-2-iodobenzene | HCID 2782750 | — |
| Reactant | 4-((Methylamino)sulphonyl)benzene boronic acid | HCID 44118763 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86723252 | HCID 86723252 | 67% |
Reaction Steps
To a solution of 4-bromo-1-fluoro-2-iodobenzene (207 mg, 0.69 mmol) in anhydrous dioxane (3.4 mL) was added [4-(methylsulfamoyl)phenyl]boronic acid (148 mg, 0.69 mmol) and aqueous Na2CO3 solution (2M, 1.03 mL, 2.06 mmol). A stream of nitrogen gas was bubbled through the reaction mixture for 6 minutes. Tetrakistriphenylphosphine palladium(0) (24 mg, 0.021 mmol) was added and the mixture was heated under microwave irradiation at 120° C. for 12 minutes. The reaction mixture was cooled, diluted with EtOAc, treated with anhydrous Na2SO4 and filtered, washing the solids with EtOAc until the compound had completely eluted. The filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with heptane:EtOAc 100:0 to 60:40 to afford the title compound as clear, colorless residue in 67% yield, 159 mg.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08952008B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-c79d085c845a427893aa7ddb043b1bfe |
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| Source note | uspto-grants-2015_02 |
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