4-Bromo-2-hydroxypyridine → 4-Bromo-2-(3-methoxypropoxy)pyridine

HRID 252355Notes

Reaction equation

HRID 252355 reaction equation
I[CH2:2][CH2:3][CH2:4][O:5][CH3:6].[Br:7][C:8]1[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=1>C1C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[Br:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:2][CH2:3][CH2:4][O:5][CH3:6])[CH:9]=1

Participants

5

Reactant 2

HCID 8171154-Bromo-2-hydroxypyridineHCID 135229891-Iodo-3-methoxypropane

Product 1

HCID 231494694-Bromo-2-(3-methoxypropoxy)pyridine

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 241BenzeneSolvent

Conditions

Temperature
45 °C

Procedure

11 mmol of silver carbonate and 20 mmol of 1-iodo-3-methoxypropane [61542-10-7] are added under an argon atmosphere to a solution of 21 mmol of 4-bromo-1H-pyridin-2-one [36953-37-4] in 30 ml of benzene. The reaction mixture is heated to 45° C. with exclusion of light for 2 days. The mixture is cooled to room temperature and filtered through Hyflo. The filtercake is washed with benzene and with saturated aqueous sodium hydrogencarbonate solution. The phases of the filtrate are separated and the aqueous phase is extracted with dichloromethane (3×). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value by means of flash chromatography (SiO2 60F).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationfiltered through Hyflo
  3. washThe filtercake is washed with benzene and with saturated aqueous sodium hydrogencarbonate solution
  4. customThe phases of the filtrate are separated
  5. extractionthe aqueous phase is extracted with dichloromethane (3×)
  6. dry with materialThe combined organic phases are dried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5d5145d6c9154d2faefc3380389083d5
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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