Water → 5-Bromo-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl ester

HRID 632182Notes

Reaction equation

HRID 632182 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]([OH:15])=[O:14])=[N:6][C:7]=1[O:8][CH2:9][CH2:10][O:11][CH3:12].IC.[C:18](=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C>[CH3:18][O:14][C:13]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[C:7]([O:8][CH2:9][CH2:10][O:11][CH3:12])[N:6]=1)=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 710877515-Bromo-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid

Product 1

HCID 710877995-Bromo-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl esterYield 66.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromo-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid (2.48 g, 9 mmol), iodomethane (2.55 g, 18 mmol) and sodium carbonate (0.106 g, 9 mmol) in DMF (30 mL) was stirred overnight at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed three times with brine, dried (sodium sulfate) and evaporated. The residue was purified by column chromatography (silica gel, 50 g, 30% ethyl acetate in petroleum ether) to yield the title compound (1.7 g, 6 mmol, 65%) as yellow solid; MS (EI): m/e 290.0 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organic extracts were washed three times with brine
  3. dry with materialdried (sodium sulfate)
  4. customevaporated
  5. customThe residue was purified by column chromatography (silica gel, 50 g, 30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-7c301d90aacb45d6b2da0efb7702b3f7
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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