Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 5-Bromopyridine-2-carbonitrile | HCID 817154 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 58181278 | HCID 58181278 | — |
Reaction Steps
A solution of 500 mg (2.73 mmol) 5-bromopicolinonitrile, 63 mg (0.07 mmol) Pd2 dba3 and 130 mg (0.27 mmol) 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl in 20 ml DME was stirred and degassed with N2 for 10 min. 1.45 g (6.83 mmol) K3PO4 and 297 μl (3.0 mmol) piperidine were added. The mixture was heated at 80° C. under N2 over night. The mixture was cooled to r.t. and filtered through a plug of SiO2 with CH2Cl2/MeOH 9:1. The filtrate was concentrated and purified by flash chromatography (SiO2, Pet. ether/EtOAc 4:1→1:1) to afford 323 mg (63%, yellow oil).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08415333B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-22009cc7c9da4329ab05c405c95cd959 |
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| Source note | uspto-grants-2013_04 |
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