Methyl iodide → 3-Bromo-6-methoxypicolinonitrile

HRID 1479485Notes

Reaction equation

HRID 1479485 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]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 668751023-Bromo-6-oxo-1,6-dihydropyridine-2-carbonitrile

Product 1

HCID 534856273-Bromo-6-methoxypicolinonitrile

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

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

  1. customdark at room temperature
  2. customovernight
  3. concentrationThe solvent was concentrated en vacuo
  4. 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…