Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | 6-Chloro-2-picoline | HCID 87601 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | 3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidine | HCID 59453372 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 87158436 | HCID 87158436 | 66.2% |
Reaction Steps
2-Chloro-6-methylpyridine (1.6 g), 3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-pyrrolidine (4.0 g), sodium t-butoxide (1.5 g), tris(dibenzylidenacetone)dipalladium (0)-chloroform adduct (0.2 g) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.25 g) were added to toluene (15 ml), and heated for 1 hour at 120° C. using a microwave reactor (trade name: INITIATOR™, manufactured by Biotage). Upon the completion of the reaction, the reaction mixture was diluted with ethyl acetate, and the precipitate was filtered off through a short silica gel layer. The filtrate was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 2-methyl-6-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]pyridine (3.4 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09375000B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-52147bf372654aacb159a2691e12096b |
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| Source note | uspto-grants-2016_06 |
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