Water → 5-Bromo-6-methylpyridine-2-carbonitrile
Reaction equation
[C-:1]#[N:2].[Na+].[Br:4][C:5]1[C:6]([CH3:12])=[N:7][C:8](F)=[CH:9][CH:10]=1.O>CS(C)=O>[Br:4][C:5]1[CH:10]=[CH:9][C:8]([C:1]#[N:2])=[N:7][C:6]=1[CH3:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
NaCN (4 g, 82 mmol) was added to a solution of 3-bromo-6-fluoro-2-methyl-pyridine (4 g, 21 mmol) in DMSO (100 mL) The mixture was stirred for 2 h at 100° C., poured into H2O (100 mL) and extracted with ethyl acetate (2×100 mL). The organic layers were dried over Na2SO4, concentrated and purified by flash column chromatography (silica gel, 10 g, eluting with 10% ethyl acetate in petroleum ether) to give the title compound (0.6 g, 15%) as white solid; MS (D): m/e=197.0 [M+H]+.
Workup
- extractionextracted with ethyl acetate (2×100 mL)
- dry with materialThe organic layers were dried over Na2SO4
- concentrationconcentrated
- custompurified by flash column chromatography (silica gel, 10 g, eluting with 10% ethyl acetate in petroleum ether)
Sources & evidence
- ORD record
- ord-be8f97984be3426bb26a224371764105
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09290451B2
Reaction notes
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