Potassium Carbonate → Ethyl 6-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}-2-(trifluoro-methyl)nicotinate

HRID 2206921Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=1.[F:17][C:18]([F:39])([F:38])[C:19]1[CH:20]=[C:21]([C:29]2([C:34]([F:37])([F:36])[F:35])[CH2:33][CH2:32][NH:31][CH2:30]2)[CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:27][C:25]([F:26])([F:28])[C:23]1[CH:22]=[C:21]([C:29]2([C:34]([F:37])([F:35])[F:36])[CH2:33][CH2:32][N:31]([C:2]3[CH:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=3)[CH2:30]2)[CH:20]=[C:19]([C:18]([F:17])([F:38])[F:39])[CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 2-chloro-6-(trifluoromethyl)pyridin-5-carboxylate (0.95 g), 3-[3,5-bis-(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidine (1.4 g) and potassium carbonate (0.7 g) were added to N,N-dimethylformamide (30 ml), and heated for 5 hours at 100° C. After cooling, the reaction mixture was poured in ice water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, the solvent was distilled off under reduced pressure, and purified by silica gel column chromatography to obtain ethyl 6-{3-[3,5-bis-(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}-2-(trifluoromethyl)nicotinate (1.7 g).

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
custompurified by silica gel column chromatography

Sources & evidence

ORD record: ord-34b76fd80a0f4bd6ac3756f67c70aef7
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09375000B2

Reaction notes

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