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

HRID 656235Notes

Reaction equation

HRID 656235 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 113.26 mmol of 5-bromo-3-(3-methoxypropoxy)-1H-pyridin-2-one, 79.28 mmol of silver carbonate and 158.56 mmol of iodomethane in 230 ml of benzene is stirred at 45° C. with exclusion of light for 24 hours. The reaction mixture is cooled to room temperature, and the silver salts are filtered off. The filtrate is washed with 2% sodium bicarbonate solution and water (2×). The organic phase is dried over sodium sulphate and evaporated. The crude title compound is obtained as a beige oil from the residue and is employed without further purification in the next stage. Rf=0.45 (EtOAc-heptane 1:2); Rt=4.34 (Gradient I).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationthe silver salts are filtered off
  3. washThe filtrate is washed with 2% sodium bicarbonate solution and water (2×)
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-2458b09a853349989fa62fcf49c6f0e3
Source dataset
uspto-grants-2011_12
Patent number
US08071651B2

Reaction notes

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