Dimethylformamide → 2-(2-Fluoropyridin-4-YL)acetonitrile
Reaction equation
[CH3:1][N:2](C=O)C.[F:6][C:7]1[CH:12]=[C:11]([CH2:13]OS(C)(=O)=O)[CH:10]=[CH:9][N:8]=1.[C-]#N.[Na+]>C(OCC)(=O)C>[F:6][C:7]1[CH:12]=[C:11]([CH2:13][C:1]#[N:2])[CH:10]=[CH:9][N:8]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To the DMF (28 ml) solution of methanesulfonic acid (2-fluoropyridin-4-yl)methyl ester (1.16 g), sodium cyanide (0.42 g) was added and the mixture was stirred at 80° C. for 1 hr. The mixture was diluted with ethyl acetate (100 ml), and washed with 15% brine and distilled water in order. The organic layer was concentrated and purified by silica gel column (n-hexane/ethyl acetate=5/1) to obtain the title compound (278 mg, 36%).
Workup
- washwashed with 15% brine
- distillationdistilled water in order
- concentrationThe organic layer was concentrated
- custompurified by silica gel column (n-hexane/ethyl acetate=5/1)
Sources & evidence
- ORD record
- ord-71ed080e150e4c8bb0fd9e84b42f10ed
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09440922B2
Reaction notes
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