Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | 3-Bromobenzonitrile | HCID 23381 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Catalyst | (+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl | HCID 86595863 | — |
| Product | HCID 82013681 | HCID 82013681 | 58% |
Reaction Steps
3-Bromo-benzonitrile (500 mg, 2.75 mmol), benzylamine (360 μl, 3.30 mmol), 2,2-bis(diphenylphosphino)-1,1′-binaphthyl (8.6 mg, 14 μmol), tris(dibenzylideneacetone)dipalladium(0) (19 mg, 21 μmol) and sodium tert-butoxide (370 mg, 3.85 mmol) were suspended in toluene (10 mL), and the mixture was stirred at 80° C. for 22 hours under nitrogen atmosphere. The reaction mixture was filtered through Celite pad, then, the filtrate was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=15:1), and the title compound (331 mg, 1.59 mmol, 58%) was obtained as a pale yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07932272B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-8b4a80eccaaf44298d725814da782d43 |
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| Source note | uspto-grants-2011_04 |
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