Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Methylphenylacetylene | HCID 136600 | — |
| Reactant | HCID 59294388 | HCID 59294388 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86641230 | HCID 86641230 | 100.7% |
Reaction Steps
A solution of (R)-benzyl 3-(5-bromothiophene-2-sulfonamido)-4-(dimethylamino)butanoate (25 mg, 0.05 mmol) and 3-ethynyltoluene (6 mg, 0.055 mmol) in ethyl acetate (0.5 mL) and H2O (50 μL) was purged with argon. Triethylamine (15 μL, 0.1 mmol), copper iodide (0.5 mg, 0.05 eq) and Bis(triphenylphosphine)palladium(II) dichloride (0.9 mg, 0.025 eq) were added and the solution was heated to 60° C. for 2 h. The mixture was cooled and purified by silica gel chromatography (CH2Cl2 to 2% MeOH in CH2Cl2) to give the title compound as a green oil (25 mg, 92%). MS ESI 497.3 [M+H]+, calcd for [C26H28N2O4S+H]+ 497.15.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08410150B2 |
|---|
| Source dataset | uspto-grants-2013_04 |
|---|
| ORD ID | ord-1e886be3b9414e0f8b57d45dca834e35 |
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| Source note | uspto-grants-2013_04 |
|---|