Toluene → HCID 87158436, compound

HRID 2206906Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.[Cl:9][C:10]1[CH:11]=[C:12]([C:18]2([C:23]([F:26])([F:25])[F:24])[CH2:22][CH2:21][NH:20][CH2:19]2)[CH:13]=[C:14]([Cl:17])[C:15]=1[Cl:16].CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>C(OCC)(=O)C.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([N:20]2[CH2:21][CH2:22][C:18]([C:12]3[CH:13]=[C:14]([Cl:17])[C:15]([Cl:16])=[C:10]([Cl:9])[CH:11]=3)([C:23]([F:24])([F:25])[F:26])[CH2:19]2)[N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

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).

Workup

customUpon the completion of the reaction
filtrationthe precipitate was filtered off through a short silica gel layer
distillationThe filtrate was distilled off under reduced pressure
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-52147bf372654aacb159a2691e12096b
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09375000B2

Reaction notes

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