Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Bromo-5-chlorothiophene | HCID 76133 | — |
| Reactant | Tert-butyl(4-chloro-2-ethynylphenoxy)acetate | HCID 56594381 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 46865875 | HCID 46865875 | — |
Reaction Steps
A mixture of 2-bromo-5-chlorothiophene (Aldrich, 163 mg; 0.82 mmol), tert-butyl(4-chloro-2-ethynylphenoxy)acetate (Intermediate 3, 200 mg; 0.75 mmol), dichlorobis(triphenylphosphine)palladium(II) (33 mg; 0.04 mmol), copper(I) iodide (8.6 mg; 0.04 mmol) was degassed during two minutes under nitrogen then THF (3 mL) and triethylamine (208 μL; 1.50 mmol) were added and reaction mixture was stirred at 60° C. for 16 hours. The solvent was evaporated and the residue was treated with an HCl solution (4 N in dioxane, 3.7 mL). After stirring for 16 hours, the solvents were removed under vacuum and the crude product purified by preparative HPLC. The title compound was obtained as a brown sticky solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08273769B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-0810f878e39d443c89f8dcba88d4119d |
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| Source note | uspto-grants-2012_09 |
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