Ammonia → HCID 86708231, compound
Reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([F:8])([F:7])[C:4]([O-])=O.[Na+].Cl[C:13]1[CH:18]=[CH:17]C(I)=[CH:15][N:14]=1.[CH3:20][NH2:21].N.C(=O)(O)[O-].[Na+]>[Cu](I)I.C1(C)C(C)=CC=CC=1.CN1C(=O)CCC1>[CH3:20][NH:21][C:13]1[CH:18]=[CH:17][C:4]([C:3]([F:8])([F:7])[C:2]([F:10])([F:9])[F:1])=[CH:15][N:14]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 150 °C
Procedure
28 g of sodium pentafluoropropionate and 14 g of copper iodide were added to a mixture of 7.2 g of 2-chloro-5-iodopyridine, 75 mL of NMP and 75 mL of xylene under room temperature, and the mixture was heated to 150° C. and heated and stirred for 5.5 hours. After cooling the mixture to 80° C., 180 mL of a 40% aqueous methylamine solution was added in 4 parts every 2 hours, and the mixture was heated and stirred for 8.5 hours. After the reaction, the mixture was ice-cooled to 0° C., a 28% aqueous ammonia solution and a saturated aqueous sodium bicarbonate solution were added, and the mixture was extracted with MTBE. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 4.6 g of methyl-(5-pentafluoroethyl-pyridin-2-yl)-amine.
Workup
- temperatureheated
- temperatureAfter cooling the mixture to 80° C.
- temperaturethe mixture was heated
- stirringstirred for 8.5 hours
- customAfter the reaction
- temperaturecooled to 0° C.
- extractionthe mixture was extracted with MTBE
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-521aa56110924bca9f89cd62e5626127
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09392791B2
Reaction notes
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