Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | HCID 59973116 | HCID 59973116 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 9948484 | HCID 9948484 | — |
Reaction Steps
(Trimethylsilyl)acetylene (1.36 g,13.8 mmol) (Aldrich) and (Z)-5-bromo-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (2.0 g, 6.9 mmol) (Starting Material 7) were dissolved in 30 mL DMF and 40 mL triethylamine. The solution was degassed for 30 minutes by bubbling argon through the solution. At this time CuI (130 mg, 0.68 mmol) (Aldrich) and (Ph3P)2PdCl2 (400 mg, 0.57 mmol) (Aldrich) were added, and the reaction was heated, under argon, at 70° C. for 22 hours. Water (20 mL) was then added and the precipitate was filtered off and dried. The product was purified via flash column chromatography (SiO2, 230-400 mesh) with 1% MeOH/CHCl3 to give (Z)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-5-(trimethylsilyl)ethynyl-2H-indol-2-one as a yellow powder. (Yield 1.07 g, 51%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06313310B1 |
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| Source dataset | uspto-grants-2001_11 |
|---|
| ORD ID | ord-0ba02400647342e68c97ebe4d8ec0999 |
|---|
| Source note | uspto-grants-2001_11 |
|---|
