Methyl iodide → 3-Bromo-6-methoxypicolinonitrile
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](=[O:8])[NH:4][C:3]=1[C:9]#[N:10].I[CH3:12]>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[Br:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([O:8][CH3:12])=[CH:6][CH:7]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 3-bromo-6-oxo-1,6-dihydropyridine-2-carbonitrile (from Example 15/Step 2) (1.0 eq.), silver carbonate (1.3 eq.), and iodomethane (1.2 eq.) in toluene (0.2 M) was stirred in the dark at room temperature overnight. The solvent was concentrated en vacuo, and the resulting residue was purified by a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give 3-bromo-6-methoxypicolinonitrile.
Workup
- customdark at room temperature
- customovernight
- concentrationThe solvent was concentrated en vacuo
- customthe resulting residue was purified by a COMBIFLASH® system (ISCO)
Sources & evidence
- ORD record
- ord-e3e696424e214f24b0cf2023ebf5f8aa
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09408907B2
Reaction notes
Loading…