Dimethylamine → 2-(Dimethylamino)-6-(trifluoromethyl)pyridine-3-carbaldehyde
Reaction equation
Cl[C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:14][NH:15][CH3:16]>C1COCC1>[CH3:14][N:15]([CH3:16])[C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a stirred solution of 2-chloro-6-(trifluoromethyl)nicotinaldehyde (115 mg, 0.549 mmol) in THF (1 mL) was added dimethylamine (823 μl, 1.65 mmol). The reaction was heated to 50° C. and stirred for 3 hours. The reaction was loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield the desired compound (50 mg, 0.229 mmol, 41.8% yield).
Workup
- washeluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes
Sources & evidence
- ORD record
- ord-e5492b26e36846f8a75d4a64a613d23f
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785445B2
Reaction notes
Loading…