3-(Trifluoromethyl)benzylamine → 4-Pyridinecarboxamide, 2-bromo-N-[[3-(trifluoromethyl)phenyl]methyl]-
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.CCN=C=NCCCN(C)C.Cl.[F:23][C:24]([F:34])([F:33])[C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][NH2:29]>ClCCl.CN(C)C1C=CN=CC=1>[F:23][C:24]([F:33])([F:34])[C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][NH:29][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][N:10]=[C:2]([Br:1])[CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
Into a 250-mL round bottom flask, was placed a solution of 2-bromoisonicotinic acid (1.4 g, 6.93 mmol, 1.20 equiv) in dichloromethane (50 mL), EDC.HCl (1.64 g, 8.56 mmol, 1.50 equiv), 4-dimethylaminopyridine (1.04 g, 8.51 mmol, 1.50 equiv), and 3-(trifluoromethyl)benzylamine (1.0 g, 5.71 mmol, 1.00 equiv). The resulting solution was stirred overnight at 25° C. in an oil bath. The resulting solution was diluted with 100 mL of dichloromethane. The resulting mixture was washed with 2×50 mL of sat. NH4Cl, 2×50 mL of sat. Na2CO3, and 2×50 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:10-1:5). The product was obtained as 1.2 g (59%) of a white solid.
Workup
- customInto a 250-mL round bottom flask, was placed
- washThe resulting mixture was washed with 2×50 mL of sat. NH4Cl, 2×50 mL of sat. Na2CO3, and 2×50 mL of brine
- dry with materialThe mixture was dried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
- washeluted with ethyl acetate/petroleum ether (1:10-1:5)
Sources & evidence
- ORD record
- ord-5da913cb614c445f922c458ab74e98cd
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916569B2
Reaction notes
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