Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (Cyclopent-1-en-1-yl)boronic acid | HCID 3861343 | — |
| Reactant | HCID 42644851 | HCID 42644851 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 57750907 | HCID 57750907 | 69% |
Reaction Steps
2-[[(E)-2-(4-Bromophenyl)ethenylsulfonylamino]benzenesulfonamide (75 mg, 0.18 mmol), cyclopenten-1-ylboronic acid (40.2 mg, 0.36 mmol), (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (14.79 mg, 0.02 mmol) and sodium carbonate (38.1 mg, 0.36 mmol) were suspended in N,N-dimethylformamide (2 mL) and the reaction mixture was stirred under an atmosphere of argon at 90° C. for 16 hours. The reaction mixture was diluted with tetrahydrofuran and filtered through Celite. The solvent was removed in vacuo and the residue was purified by preparative HPLC. The residue was purified a second time by column chromatography, using gradient mixtures of ethyl acetate/heptane as eluent (0%-100% ethyl acetate) to give 50 mg (69% yield) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09145380B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-f5b6d663531f437aae4d6cb4437487a2 |
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| Source note | uspto-grants-2015_09 |
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