Methyl iodide → 5-Bromo-2-methoxy-3-(3-methoxypropoxy)-pyridine

HRID 252362Notes

Reaction equation

HRID 252362 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[C:5](=[O:8])[NH:6][CH:7]=1.I[CH3:16]>C1C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[C:5]([O:8][CH3:16])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 231494755-bromo-3-(3-methoxypropoxy)-1H-pyridin-2-one

Product 1

HCID 231494925-Bromo-2-methoxy-3-(3-methoxypropoxy)-pyridine

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 241BenzeneSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 21 mmol 5-bromo-3-(3-methoxy-propoxy)-1H-pyridin-2-one, 14 mmol silver carbonate and 25 mmol iodomethane in 35 ml of benzene are stirred at 40-50° C. for 24 hours with exclusion of light. The mixture is cooled in an ice bath and the silver salts are removed by filtration. The filtrate is washed with 2% aqueous sodium hydrogencarbonate solution and with water (2×). The organic layer is dried over sodium sulphate, filtered and concentrated. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) and identified based on its Rf value.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. customthe silver salts are removed by filtration
  3. washThe filtrate is washed with 2% aqueous sodium hydrogencarbonate solution and with water (2×)
  4. dry with materialThe organic layer is dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-859fe21e75bd43249bd83b7a57b50340
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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