Diisopropylethylamine → 5-iodo-N-(1-(3-methoxy-4-((4-(trifluoromethyl)benzyl)oxy)phenyl)ethyl)-3-nitropyridin-2-amine
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:21]([NH2:23])[CH3:22])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1.ClCC1C=CC(C(F)(F)F)=CC=1.C(N(CC)C(C)C)(C)C.Cl[C:46]1[C:51]([N+:52]([O-:54])=[O:53])=[CH:50][C:49]([I:55])=[CH:48][N:47]=1>C(#N)C.O>[I:55][C:49]1[CH:50]=[C:51]([N+:52]([O-:54])=[O:53])[C:46]([NH:23][CH:21]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:18])[F:20])=[CH:13][CH:12]=3)=[C:3]([O:2][CH3:1])[CH:4]=2)[CH3:22])=[N:47][CH:48]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 1-(3-methoxy-4-((4-(trifluoromethyl)benzyl)oxy)phenyl)ethanamine [prepared from 1-(chloromethyl)-4-(trifluoromethyl)benzene using the procedures described in Example 3-45-1 through Example 3-45-3] (2.52 g, 7.75 mmol) and N,N-diisopropylethylamine (2.7 mL, 15.18 mmol) in acetonitrile (30 mL) was added 2-chloro-5-iodo-3-nitropyridine (2.39 g, 8.13 mmol), The orange solution was heated to reflux. After 15 h, the brown reaction mixture was allowed to cool to room temperature and was diluted with water (60 mL). As the mixture was stirred, a yellow precipitate formed. The solids were isolated by filtration and washed with water (50 mL), and dried to provide 4.19 g (94%) of 5-iodo-N-(1-(3-methoxy-4-((4-(trifluoromethyl)benzyl)oxy)phenyl)ethyl)-3-nitropyridin-2-amine as a yellow solid.
Workup
- temperatureThe orange solution was heated to reflux
- customa yellow precipitate formed
- customThe solids were isolated by filtration
- washwashed with water (50 mL)
- customdried
Sources & evidence
- ORD record
- ord-68fc1761d42a438f97adc1b1145a5c26
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174986B2
Reaction notes
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