Methanol → Methyl 5-bromopyridine-3-carboxylate
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:11]O>>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O:9][CH3:11])=[O:8]Participants
3
Procedure
A solution of 5-bromonicotinic acid (6.65 g, 32.9 mmol) in 75 mL of MeOH was heated to reflux for 4 hours, cooled to room temperature, and concentrated in vacuo. The residue was diluted with aqueous sodium bicarbonate and EtOAc, and the organic fraction was washed with brine, dried, filtered, and concentrated in vacuo to provide crude methyl 5-bromonicotinate. To a solution of the above compound in 100 mL of THF at −70° C. was added LAH (1 M in THF, 0.036 mL, 0.036 mmol). After 1 hour, 1 mL of water and 1 mL 1 N NaOH were added, followed by 2 mL of aqueous ammonium chloride. The mixture was diluted with ether and sodium sulfate, filtered, and concentrated in vacuo to provide the title compound as a yellow oil.
Workup
- temperatureto reflux for 4 hours
- concentrationconcentrated in vacuo
- additionThe residue was diluted with aqueous sodium bicarbonate and EtOAc
- washthe organic fraction was washed with brine
- customdried
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-704af28e1c114530b899a631fb3befc0
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293914B2
Reaction notes
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