Water → Methyl 6-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)-pyrrolidin-1-yl}-4-(trifluoromethyl)nicotinate

HRID 2206914

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 6-chloro-4-(trifluoromethyl)nicotinate (2.39 g), 3-[3,5-bis(trifluoromethyl)-phenyl]-3-(tri-fluoromethyl)pyrrolidine (2.98 g) and potassium carbonate (1.8 g) were suspended in dimethylformamide (50 ml). The reaction mixture was heated for 8 hours at 80° C. Water and ethyl acetate were added and the extraction was carried out. The extract was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The target compound (3.07 g) was obtained by purification with silica gel column chromatography.

Workup

extractionthe extraction
dry with materialThe extract was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-290fb8e9b01e422cb99952c9f972d628
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09375000B2

Linked notes

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