Triethylamine → 2-Chloro-5-fluoropyridine-3-carbonitrile
Reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[N:17]=[CH:16][C:15]([F:18])=[CH:14][C:10]=1[C:11]([NH2:13])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[Cl:8][C:9]1[N:17]=[CH:16][C:15]([F:18])=[CH:14][C:10]=1[C:11]#[N:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
81.2 ml (582.25 mmol) of triethylamine were added to a suspension of 46.2 g (264.66 mmol) of 2-chloro-5-fluoronicotinamide in dichloromethane (783 ml), and the mixture was cooled to 0° C. With stirring, 41.12 ml (291.13 mmol) of trifluoroacetic anhydride were then slowly added dropwise, and the mixture was stirred at 0° C. for another 1.5 h. The reaction solution was then washed twice with saturated aqueous sodium bicarbonate solution (391 ml each), dried and concentrated under reduced pressure.
Workup
- stirringthe mixture was stirred at 0° C. for another 1.5 h
- washThe reaction solution was then washed twice with saturated aqueous sodium bicarbonate solution (391 ml each)
- customdried
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-6d86a521e6d0413fa0c445092922045f
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09216978B2
Reaction notes
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