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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2206906Generated: October 30, 2026

Toluene → HCID 87158436, compound

https://huagongshe.com/reaction/2206906

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
Reactant6-Chloro-2-picolineHCID 87601—
ReactantSodium t-butoxideHCID 23676156—
Reactant3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidineHCID 59453372—
Catalyst1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 636044—
SolventEthyl AcetateHCID 8857—
ProductHCID 87158436HCID 8715843666.2%

Reaction Conditions

Temperature120 °C

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09375000B2
Source datasetuspto-grants-2016_06
ORD IDord-52147bf372654aacb159a2691e12096b
Source noteuspto-grants-2016_06