Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 4-(Trifluoromethyl)benzylamine | HCID 76804 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | HCID 86651745 | HCID 86651745 | — |
| Catalyst | HCID 178439030 | HCID 178439030 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 67058147 | HCID 67058147 | 6% |
Reaction Steps
2-Bromo-5-(1,3,3-triethoxypropyl)pyridine (328 mg, 0.987 mmol) produced in Example 17 (17B) and 4-trifluoromethylbenzylamine (346 mg, 1.98 mmol) were dissolved in 1,2-dimethoxyethane (10 mL), and potassium tert-butoxide (346 mg, 1.98 mmol) and [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) (34 mg, 5 mol %) were added thereto, and then, the resulting mixture was stirred under a nitrogen atmosphere at 100° C. for 3 hours. After the reaction solution was cooled to room temperature, water was added thereto, and the organic matter was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 50:50 (v/v)), whereby the objective title compound was obtained as a colorless oily substance (25 mg, yield: 6%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08222281B2 |
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| Source dataset | uspto-grants-2012_07 |
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| ORD ID | ord-d5162fd27ad54ffdbb22e89324a82bb0 |
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| Source note | uspto-grants-2012_07 |
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