Methyl iodide → Methyl 6-bromo-3-methoxypyridine-2-carboxylate

HRID 595551Notes

Reaction equation

HRID 595551 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([OH:12])=[CH:4][CH:3]=1.CI.[C:15]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][CH3:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22175135Methyl 6-bromo-3-hydroxypicolinate

Product 1

HCID 70700803Methyl 6-bromo-3-methoxypyridine-2-carboxylateYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 6-bromo-3-hydroxypicolinate (4 g, 17.2 mmol), CH3I (7.15 g, 34.5 mmol) and K2CO3 (4.76 g, 34.5 mmol) in DMF (50 mL) was stirred at RT for 3 hours. After concentrated, the mixture was diluted with H2O and extracted with EtOAc (50 mL*3). The organic layer was dried over Na2SO4 and concentrated to give crude methyl 6-bromo-3-methoxypicolinate (4 g, yield: 90%). 1H-NMR (CDCl3, 400 MHz) δ 7.56 (d, J=8.0 Hz, 1H), 7.25 (d, J=8.0 Hz, 1H), 3.94 (s, 3H), 3.90 (s, 3H). MS (M+H)+: 256/258.

Workup

  1. concentrationAfter concentrated
  2. additionthe mixture was diluted with H2O
  3. extractionextracted with EtOAc (50 mL*3)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-aaa1e567019d410b971b07039e2d55d9
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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