Ammonia → 5-(Trifluoromethyl)pyridine-2,3-diamine
Reaction equation
Br[C:2]1[C:3]([NH2:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(CC(=O)C)(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[NH3:26]>O.[Cu+2].C(CC(=O)C)(=O)C.CN1C(=O)CCC1>[F:9][C:8]([F:11])([F:10])[C:6]1[CH:7]=[C:2]([NH2:26])[C:3]([NH2:12])=[N:4][CH:5]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 110 °C
Procedure
To an autoclave reactor, 3-bromo-5-trifluoromethyl-pyridine-2-ylamine (40 g), acetylacetone copper(II) (2.2 g), acetylacetone (6.6 g), cesium carbonate (59 g), and NMP (105 mL) were added, and then 28% of aqueous ammonia solution (25 mL) was added under ice-cooling. After the reactor was sealed, the mixture heated to 110° C., and stirred with heating for 12 hours. The mixture was ice-cooled to room temperature, then diluted with water, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 15 g 5-trifluoromethyl-pyridine-2,3-diamine (Compound (1F)-22).
Workup
- temperaturecooling
- customAfter the reactor was sealed
- temperaturewith heating for 12 hours
- temperaturecooled to room temperature
- extractionextracted with ethyl acetate
- dry with materialThe combined organic layer was dried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-baacb3021ffb41a59b343d3555b382fb
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853238B2
Reaction notes
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