Reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([C:13]2([C:18]([F:21])([F:20])[F:19])[CH2:17][CH2:16][NH:15][CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[Br:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27](Br)[N:26]=1.C(N(CC)C(C)C)(C)C.CC(N(C)C)=O>C(OCC)(=O)C>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]2([C:18]([F:21])([F:19])[F:20])[CH2:17][CH2:16][N:15]([C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([Br:24])[N:26]=3)[CH2:14]2)[CH:4]=[C:3]([C:2]([F:22])([F:1])[F:23])[CH:8]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidine (3.0 g), 2,6-dibromopyridine (2.22 g), N,N-diisopropylethylamine (2.2 g) and dimethylacetamide (15 ml) was reacted at 160° C. in a sealed tube for 1 hour. Upon the completion of the reaction, the mixture was added with ethyl acetate, washed with water and then saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography to obtain 2-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}-6-bromopyridine (4.0 g).
Workup
- customwas reacted at 160° C. in a sealed tube for 1 hour
- customUpon the completion of the reaction
- washwashed with water
- dry with materialsaturated brine, dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-2b8d32244fdf469d902e787cde430c9e
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09375000B2
Linked notes
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