Trifluoroacetic anhydride → 2-Chloro-5-(trifluoromethyl)nicotinonitrile
Reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([NH2:6])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([C:11]([F:14])([F:12])[F:13])=[CH:7][C:3]=1[C:4]#[N:6]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-chloro-5-(trifluoromethyl)nicotinamide (as prepared in the previous step, 788 mg, 3.51 mmol) in dry DCM was added TEA (1.1 mL, 7.89 mmol). After cooling to 0° C. under argon, trifluoroacetic anhydride (0.54 mL, 3.88 mmol) was added dropwise. After stirring for 1.5 hours at 0° C., DCM (30 mL) and saturated aqueous sodium bicarbonate were introduced. The organic layer was removed and concentrated in vacuo. The resulting residue was purified by flash chromatography (silica gel, DCM) to afford the product as a tan solid.
Workup
- customThe organic layer was removed
- concentrationconcentrated in vacuo
- customThe resulting residue was purified by flash chromatography (silica gel, DCM)
Sources & evidence
- ORD record
- ord-748b7e15e1e9435ba4bbb6c7f73524cb
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08436023B2
Reaction notes
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