Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Styrene | HCID 7501 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | 5-Bromonicotinonitrile | HCID 736793 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67047630 | HCID 67047630 | 34% |
Reaction Steps
Add tris(dibenzylideneacetone)dipalladium (125 mg, 0.136 mmol) and tri-o-tolylphosphine (86 mg, 0.273 mmol) to a solution of triethylamine (0.77 mL, 5.46 mmol), 5-bromonicotinonitrile (500 mg, 2.73 mmol) and styrene (0.48 mL, 4.1 mmol) in anhydrous N,N-dimethylformamide (10 mL) under an inert atmosphere, and stir at 100° C. for 3.5 h. Cool to room temperature, add water and extract three times with diethyl ether. Combine the organic layers, dry (sodium sulfate), filter, and concentrate. Purify the residue by silica gel chromatography, eluting with dichloromethane, to give the title compound as a white solid (190 mg, 34%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07915424B2 |
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| Source dataset | uspto-grants-2011_03 |
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| ORD ID | ord-8324edd1a6c843be92bdf6e9067462be |
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| Source note | uspto-grants-2011_03 |
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