Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | 2-Cyano-6-(trifluoromethyl)pyridine | HCID 21696618 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67235870 | HCID 67235870 | 89% |
Reaction Steps
A solution of 2.08 ml (13.07 mmol) diisopropylamine in dry THF (12 ml) was cooled to −70° C. under inert gas atmosphere, and 9.26 ml (14.8 mmol) n-butyllithium solution (1.6 M in hexanes) were added dropwise. Then, a solution of 688 μl (13.07 mmol) acetonitrile in dry THF (10 ml) was slowly added over 10 min. The resulting solution was stirred for further 30 min at −70° C. before a solution of 1.50 g (8.72 mmol) 6-(trifluoromethyl)pyridine-2-carbonitrile in dry THF (10 ml) was added. The mixture was allowed to warm to room temperature and stirred for 12 h before water (200 ml) was added slowly. The mixture was extracted several times with dichloromethane (100 ml). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to yield 1.2 g (57% of th.) of the crude title compound (89% purity) which was used in the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09018234B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-fa430c645b0249c9b76d668503ac7efd |
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| Source note | uspto-grants-2015_04 |
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