2,6-Dichloropyridine → (S)-6-Chloro-N-[1-(4-fluorophenyl)ethyl]pyridine-2-amine
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]([NH2:18])[CH3:17])=[CH:12][CH:11]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+]>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[Cl:8][C:4]1[N:3]=[C:2]([NH:18][C@H:16]([C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)[CH3:17])[CH:7]=[CH:6][CH:5]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 85 °C
Procedure
300 mg of 2,6-dichloropyridine, 296 mg of (S)-(−)-1-(4-fluorophenyl)ethylamine, 119 mg of 2-(di-t-butylphosphino)biphenyl, 487 mg of sodium t-butoxide and 45 mg of palladium acetate were added in turn to 6 ml of degassed toluene, and the mixture was stirred at 85° C. for 2 hours under argon atmosphere. The reaction solution was diluted with ethyl acetate. The solution was washed in turn with water and brine and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 210 mg of the objective compound as pale yellow oil.
Workup
- washThe solution was washed in turn with water and brine
- dry with materialdried over magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe obtained residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-8c24360d3d52432bbdf13f3a650dea34
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586591B2
Reaction notes
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