Hydrochloric Acid → 5-Bromo-6-cyanopicolinic acid
Reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([C:12]#[N:13])[N:6]=1)=[O:4].Cl>C1COCC1>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]=1[C:12]#[N:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of potassium trimethylsilanoate (0.80 g, 6.22 mmol) in THF (26 mL) was added 5-bromo-6-cyano-pyridine-2-carboxylic acid methyl ester (998 mg, 4.15 mmol). The mixture was heated at 50° C. for 3 h, then was cooled to rt and treated with HCl (4 N in dioxane; 1.60 mL). After 30 min, the mixture was concentrated. The residue was dissolved in hot EtOAc and filtered. The filtrate was concentrated to give the title compound (993 mg, >100%), which was used in the next step without further purification.
Workup
- temperaturewas cooled to rt
- concentrationthe mixture was concentrated
- dissolutionThe residue was dissolved in hot EtOAc
- filtrationfiltered
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-91c71256c99440658fb70c75f9f02a8f
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637520B2
Reaction notes
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