Toluene → HCID 58181365, compound
Reaction equation
CC(C)([O-])C.[Na+].Br[C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1.C1(C)C=CC=CC=1.[CH3:22][NH:23][CH2:24][CH3:25]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].C(OCC)(=O)C>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([N:23]([CH2:24][CH3:25])[CH3:22])=[N:9][CH:10]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
To a mixture of 4,5-bis(diphenylphosphino)-9,9′-dimethylxanthene (293 mg, 0.51 mmol), tris(dibenzylideneacetone)dipalladium (0)-chloroform adduct (174 mg, 0.17 mmol), sodium t-butoxide (974 mg, 10.0 mmol), 2,5-dibromopyridine (2.0 g, 8.44 mmol) and anhydrous toluene (30 ml) was added N-methylethylamine (1.09 ml, 12.7 mmol). The mixture was heated to 70° C., and the mixture was stirred for 3 hrs. The reaction mixture was cooled to room temperature, ethyl acetate was added, and the mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19) to give 5-bromo-N-ethyl-N-methylpyridin-2-amine (1.21 g, yield 66%) as a yellow oil.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- washthe mixture was washed with water and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19)
Sources & evidence
- ORD record
- ord-d4c6849d1b714b28b01f4b81c59c3e76
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999989B2
Reaction notes
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