Methyl iodide → (5-Bromo-6-hydroxy-pyridin-3-yl)-acetic acid ethyl ester

HRID 554655Notes

Reaction equation

HRID 554655 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([O:13]C)=[C:10]([Br:12])[CH:11]=1)[CH3:2].IC>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([OH:13])=[C:10]([Br:12])[CH:11]=1)[CH3:2]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 58539686Ethyl 5-bromo-6-methoxy-3-pyridineacetate

Product 1

HCID 178470737(5-Bromo-6-hydroxy-pyridin-3-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
55 °C

Procedure

(5-Bromo-6-methoxy-pyridin-3-yl)-acetic acid ethyl ester (5.02 mmol) was dissolved in CHCl3 (17 mL). Silver carbonate (1.58 g, 5.7 mmol) and iodomethane (0.82 mL, 13.14 mmol) were added, and the reaction was stirred at 55° C. for 2.5 hours. The mixture was filtered through Celite, and the filtrate was concentrated and purified by silica gel chromatography (0-60% EtOAc in hexanes) to give (5-bromo-6-hydroxy-pyridin-3-yl)-acetic acid ethyl ester.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. custompurified by silica gel chromatography (0-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7448f2e808114f2abd30cf986c23124b
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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