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. Then, while stirring, 41.12 ml (291.13 mmol) of trifluoroacetic anhydride were slowly added dropwise and the mixture was stirred at 0° C. for 1.5 h. The reaction solution was subsequently washed twice with saturated aqueous sodium hydrogencarbonate solution (391 ml each time), dried and concentrated under reduced pressure.
Workup
- stirringthe mixture was stirred at 0° C. for 1.5 h
- washThe reaction solution was subsequently washed twice with saturated aqueous sodium hydrogencarbonate solution (391 ml each time)
- customdried
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-3c5dbd50b6e14b49a2e89da1895070d2
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765769B2
Reaction notes
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